NPASS Compound

Structure

CID128265 OpenBabel06191715482D 26 30 0 0 1 0 0 0 0 0999 V2000 5.0737 0.9433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1219 2.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5164 -1.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5162 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 -1.9369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6775 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6777 -1.9376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5163 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6783 0.9679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3551 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 2.9040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1941 1.4514 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8388 -1.4529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8387 -1.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5170 1.4519 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3554 0.9675 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5172 2.4201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 -0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6780 -0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8389 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6376 2.9283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5165 -0.4847 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.6379 3.9442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7577 2.4206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1943 2.4197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 2 0 0 0 0 6 18 2 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 23 1 0 0 0 0 9 19 1 0 0 0 0 10 23 1 0 0 0 0 11 17 2 0 0 0 0 11 26 1 0 0 0 0 12 1 1 6 0 0 0 12 16 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 20 2 0 0 0 0 15 9 1 6 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 10 1 6 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 23 1 6 0 0 0 20 22 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.18
Volume:	361.535
LogP:	3.812
LogD:	3.541
LogS:	-3.18
# Rotatable Bonds:	2
TPSA:	54.56
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.801
Synthetic Accessibility Score:	3.936
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.906
MDCK Permeability:	3.116427978966385e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.343
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.622
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	82.10932159423828%
Volume Distribution (VD):	2.113
Pgp-substrate:	12.432914733886719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.945
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.884
CYP2C19-substrate:	0.78
CYP2C9-inhibitor:	0.745
CYP2C9-substrate:	0.449
CYP2D6-inhibitor:	0.931
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.874

ADMET: Excretion

Clearance (CL):	4.938
Half-life (T1/2):	0.393

ADMET: Toxicity

hERG Blockers:	0.882
Human Hepatotoxicity (H-HT):	0.572
Drug-inuced Liver Injury (DILI):	0.531
AMES Toxicity:	0.931
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.866
Carcinogencity:	0.968
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.986

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC128265

Natural Product ID:	NPC128265
*Common Name:**	Rauniticine
IUPAC Name:	n.a.
Synonyms:	Rauniticine
Standard InCHIKey:	GRTOGORTSDXSFK-OYWVLEMYSA-N
Standard InCHI:	InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15+,16+,19+/m1/s1
SMILES:	COC(=O)C1=CO[C@@H]([C@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486933
PubChem CID:	72338
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001786] Yohimbine alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12932131]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20460582]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25172746]
NPO22126	Penicillium funiculosum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27359163]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8910532]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO4763	Uncaria elliptica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9077	Uncaria lanosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10088	Uncaria attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22083	Rauvolfia nitida	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10088	Uncaria attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12216	Gynura elliptica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4763	Uncaria elliptica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14590	Ruta oreojasme	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1603	Monostroma nitidum	Species	Monostromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22083	Rauvolfia nitida	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9077	Uncaria lanosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14590	Ruta oreojasme	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22083	Rauvolfia nitida	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25628.1	Abrus pulchellus subsp. cantoniensis	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16419	Rumex chalepensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9282	Stereocaulon colensoi	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11596	Lomatia ilicifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO907	Dictyostelium purpureum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10334	Andropogon polyneuros	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1409	Drymonia macrophylla	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11862	Ostrinia nubilalis	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4763	Uncaria elliptica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10088	Uncaria attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19160	Klasea quinquefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2065	Eriostemon deserti	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14694	Sickingia williamsii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14210	Brugmansia arborea	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13601	Relicina connivens	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25628.1	Abrus pulchellus subsp. cantoniensis	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2296	Agaricus arvensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22126	Penicillium funiculosum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19809	Streptomyces roseoviolaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21627	Bambusa chungii	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12216	Gynura elliptica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16419	Rumex chalepensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6602	Vinca major	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3078	Gentiana pyrenaica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10499	Haplopappus paucidentatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6849	Lomatia arborescens	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1603	Monostroma nitidum	Species	Monostromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9077	Uncaria lanosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25599	Gloxinia erinoides	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13490	Diospyros tricolor	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10315	Cestrum parqui	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14590	Ruta oreojasme	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3254	Fusarium caucasicum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4468	Cuspidaria pterocarpa	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[509498]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC128265 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	1411
0.2-0.3	7072
0.3-0.4	19549
0.4-0.5	9046
0.5-0.6	2561
0.6-0.7	2181
0.7-0.8	480
0.8-0.85	54
0.85-0.9	33
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC312870
1.0	High Similarity	NPC294909
1.0	High Similarity	NPC254240
1.0	High Similarity	NPC199851
0.9435	High Similarity	NPC196251
0.9435	High Similarity	NPC111602
0.9435	High Similarity	NPC63199
0.9435	High Similarity	NPC102338
0.9274	High Similarity	NPC472112
0.9263	High Similarity	NPC221100
0.9263	High Similarity	NPC234078
0.9066	High Similarity	NPC472113
0.8967	High Similarity	NPC19692
0.8967	High Similarity	NPC220151
0.8919	High Similarity	NPC245916
0.8895	High Similarity	NPC238457
0.8894	High Similarity	NPC21638
0.8785	High Similarity	NPC258480
0.8782	High Similarity	NPC82070
0.8737	High Similarity	NPC52254
0.8696	High Similarity	NPC175474
0.8587	High Similarity	NPC66210
0.8586	High Similarity	NPC476114
0.8564	High Similarity	NPC475271
0.8534	High Similarity	NPC81654
0.8534	High Similarity	NPC249150
0.8534	High Similarity	NPC195461
0.8534	High Similarity	NPC49196
0.8534	High Similarity	NPC313985
0.8534	High Similarity	NPC79129
0.8526	High Similarity	NPC52557
0.8492	Intermediate Similarity	NPC152768
0.8492	Intermediate Similarity	NPC148183
0.8429	Intermediate Similarity	NPC50503
0.8408	Intermediate Similarity	NPC174788
0.8333	Intermediate Similarity	NPC472107
0.8333	Intermediate Similarity	NPC79062
0.8324	Intermediate Similarity	NPC472108
0.8324	Intermediate Similarity	NPC139291
0.8315	Intermediate Similarity	NPC469896
0.8307	Intermediate Similarity	NPC472097
0.828	Intermediate Similarity	NPC472119
0.8245	Intermediate Similarity	NPC472323
0.8235	Intermediate Similarity	NPC472099
0.8226	Intermediate Similarity	NPC143533
0.822	Intermediate Similarity	NPC472210
0.822	Intermediate Similarity	NPC81802
0.822	Intermediate Similarity	NPC247735
0.822	Intermediate Similarity	NPC472295
0.822	Intermediate Similarity	NPC269886
0.8216	Intermediate Similarity	NPC15840
0.8212	Intermediate Similarity	NPC271797
0.8212	Intermediate Similarity	NPC21174
0.8182	Intermediate Similarity	NPC474905
0.8168	Intermediate Similarity	NPC55493
0.8158	Intermediate Similarity	NPC314333
0.8134	Intermediate Similarity	NPC33949
0.8128	Intermediate Similarity	NPC472104
0.8119	Intermediate Similarity	NPC472291
0.8108	Intermediate Similarity	NPC234987
0.8065	Intermediate Similarity	NPC219336
0.8063	Intermediate Similarity	NPC329858
0.8043	Intermediate Similarity	NPC472123
0.8032	Intermediate Similarity	NPC472110
0.8032	Intermediate Similarity	NPC472109
0.803	Intermediate Similarity	NPC476115
0.8011	Intermediate Similarity	NPC15573
0.8011	Intermediate Similarity	NPC217372
0.8011	Intermediate Similarity	NPC183662
0.7981	Intermediate Similarity	NPC473105
0.7979	Intermediate Similarity	NPC472292
0.7969	Intermediate Similarity	NPC469470
0.7969	Intermediate Similarity	NPC469501
0.7949	Intermediate Similarity	NPC472116
0.7949	Intermediate Similarity	NPC472293
0.7919	Intermediate Similarity	NPC472296
0.7919	Intermediate Similarity	NPC472297
0.7914	Intermediate Similarity	NPC326575
0.7906	Intermediate Similarity	NPC478077
0.7892	Intermediate Similarity	NPC264176
0.7889	Intermediate Similarity	NPC162730
0.7884	Intermediate Similarity	NPC113626
0.788	Intermediate Similarity	NPC317430
0.7879	Intermediate Similarity	NPC214428
0.7861	Intermediate Similarity	NPC24594
0.7861	Intermediate Similarity	NPC472122
0.785	Intermediate Similarity	NPC474192
0.785	Intermediate Similarity	NPC475720
0.7849	Intermediate Similarity	NPC161861
0.7828	Intermediate Similarity	NPC241024
0.7826	Intermediate Similarity	NPC305984
0.7824	Intermediate Similarity	NPC57453
0.7806	Intermediate Similarity	NPC289299
0.7806	Intermediate Similarity	NPC57994
0.7805	Intermediate Similarity	NPC472098
0.78	Intermediate Similarity	NPC474116
0.7772	Intermediate Similarity	NPC277350
0.7737	Intermediate Similarity	NPC187827
0.7737	Intermediate Similarity	NPC472105
0.7734	Intermediate Similarity	NPC477065
0.7717	Intermediate Similarity	NPC475816
0.7713	Intermediate Similarity	NPC329688
0.7713	Intermediate Similarity	NPC189812
0.771	Intermediate Similarity	NPC311906
0.7703	Intermediate Similarity	NPC473041
0.7703	Intermediate Similarity	NPC96321
0.7659	Intermediate Similarity	NPC477548
0.7644	Intermediate Similarity	NPC91179
0.7644	Intermediate Similarity	NPC477979
0.7642	Intermediate Similarity	NPC191489
0.7632	Intermediate Similarity	NPC28848
0.7632	Intermediate Similarity	NPC145885
0.7632	Intermediate Similarity	NPC14113
0.7632	Intermediate Similarity	NPC84827
0.7632	Intermediate Similarity	NPC14325
0.7629	Intermediate Similarity	NPC62749
0.7629	Intermediate Similarity	NPC160381
0.7619	Intermediate Similarity	NPC281049
0.7609	Intermediate Similarity	NPC81229
0.7609	Intermediate Similarity	NPC255229
0.7598	Intermediate Similarity	NPC284685
0.7588	Intermediate Similarity	NPC102592
0.7588	Intermediate Similarity	NPC79356
0.7586	Intermediate Similarity	NPC165599
0.7586	Intermediate Similarity	NPC100734
0.7586	Intermediate Similarity	NPC88923
0.7586	Intermediate Similarity	NPC315634
0.7581	Intermediate Similarity	NPC478078
0.7571	Intermediate Similarity	NPC312645
0.7549	Intermediate Similarity	NPC132539
0.7548	Intermediate Similarity	NPC118940
0.7538	Intermediate Similarity	NPC474121
0.7538	Intermediate Similarity	NPC235684
0.7536	Intermediate Similarity	NPC471304
0.7535	Intermediate Similarity	NPC472762
0.7525	Intermediate Similarity	NPC249040
0.7524	Intermediate Similarity	NPC330009
0.7524	Intermediate Similarity	NPC469928
0.7513	Intermediate Similarity	NPC71037
0.7512	Intermediate Similarity	NPC89508
0.75	Intermediate Similarity	NPC476098
0.7487	Intermediate Similarity	NPC267885
0.7474	Intermediate Similarity	NPC21752
0.7474	Intermediate Similarity	NPC19679
0.7474	Intermediate Similarity	NPC181138
0.7474	Intermediate Similarity	NPC210415
0.7474	Intermediate Similarity	NPC298851
0.7474	Intermediate Similarity	NPC276993
0.7474	Intermediate Similarity	NPC293255
0.7473	Intermediate Similarity	NPC194881
0.7453	Intermediate Similarity	NPC303658
0.7452	Intermediate Similarity	NPC126066
0.7452	Intermediate Similarity	NPC234999
0.7451	Intermediate Similarity	NPC476874
0.7435	Intermediate Similarity	NPC203468
0.7435	Intermediate Similarity	NPC110500
0.7435	Intermediate Similarity	NPC149155
0.7426	Intermediate Similarity	NPC306376
0.7426	Intermediate Similarity	NPC67288
0.7412	Intermediate Similarity	NPC473800
0.7409	Intermediate Similarity	NPC133261
0.7409	Intermediate Similarity	NPC248041
0.7409	Intermediate Similarity	NPC126709
0.7407	Intermediate Similarity	NPC78020
0.7404	Intermediate Similarity	NPC478158
0.7404	Intermediate Similarity	NPC469743
0.7402	Intermediate Similarity	NPC471944
0.7401	Intermediate Similarity	NPC88097
0.7398	Intermediate Similarity	NPC133003
0.7396	Intermediate Similarity	NPC264482
0.7396	Intermediate Similarity	NPC203202
0.7391	Intermediate Similarity	NPC244741
0.7391	Intermediate Similarity	NPC53344
0.7389	Intermediate Similarity	NPC74413
0.7387	Intermediate Similarity	NPC184680
0.7385	Intermediate Similarity	NPC66777
0.7381	Intermediate Similarity	NPC475778
0.7376	Intermediate Similarity	NPC141454
0.7371	Intermediate Similarity	NPC469594
0.7366	Intermediate Similarity	NPC260900
0.736	Intermediate Similarity	NPC315555
0.736	Intermediate Similarity	NPC311858
0.736	Intermediate Similarity	NPC141612
0.736	Intermediate Similarity	NPC17273
0.736	Intermediate Similarity	NPC135601
0.7358	Intermediate Similarity	NPC111275
0.7356	Intermediate Similarity	NPC475910
0.7354	Intermediate Similarity	NPC470785
0.7354	Intermediate Similarity	NPC470784
0.7353	Intermediate Similarity	NPC329793
0.7351	Intermediate Similarity	NPC285469
0.7349	Intermediate Similarity	NPC60621
0.7347	Intermediate Similarity	NPC228835
0.7346	Intermediate Similarity	NPC229348
0.7346	Intermediate Similarity	NPC469592
0.7346	Intermediate Similarity	NPC471080
0.7343	Intermediate Similarity	NPC472111
0.7343	Intermediate Similarity	NPC18661
0.7342	Intermediate Similarity	NPC477549
0.7339	Intermediate Similarity	NPC476491

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC128265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	500
0.2-0.3	669
0.3-0.4	1481
0.4-0.5	2670
0.5-0.6	2659
0.6-0.7	883
0.7-0.8	105
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4500	Approved
1.0	High Similarity	NPD4501	Approved
0.8534	High Similarity	NPD4601	Approved
0.8534	High Similarity	NPD4600	Approved
0.8158	Intermediate Similarity	NPD4499	Approved
0.7837	Intermediate Similarity	NPD6770	Approved
0.7833	Intermediate Similarity	NPD4506	Discontinued
0.7806	Intermediate Similarity	NPD4602	Approved
0.7778	Intermediate Similarity	NPD3393	Approved
0.7778	Intermediate Similarity	NPD3389	Approved
0.7778	Intermediate Similarity	NPD3394	Approved
0.7696	Intermediate Similarity	NPD2509	Approved
0.7696	Intermediate Similarity	NPD2510	Approved
0.7672	Intermediate Similarity	NPD5104	Approved
0.765	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7708	Approved
0.7633	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7956	Approved
0.7598	Intermediate Similarity	NPD7955	Approved
0.7586	Intermediate Similarity	NPD6176	Phase 1
0.7586	Intermediate Similarity	NPD7803	Approved
0.7581	Intermediate Similarity	NPD2915	Discontinued
0.7565	Intermediate Similarity	NPD2095	Phase 2
0.7565	Intermediate Similarity	NPD2094	Phase 2
0.7565	Intermediate Similarity	NPD2092	Phase 2
0.755	Intermediate Similarity	NPD5003	Discontinued
0.7526	Intermediate Similarity	NPD2096	Phase 2
0.7526	Intermediate Similarity	NPD2091	Phase 2
0.75	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD6249	Phase 2
0.7475	Intermediate Similarity	NPD6248	Phase 2
0.7475	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4885	Approved
0.7438	Intermediate Similarity	NPD6479	Discontinued
0.7435	Intermediate Similarity	NPD482	Approved
0.7407	Intermediate Similarity	NPD2844	Phase 3
0.7398	Intermediate Similarity	NPD5075	Discontinued
0.7396	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5901	Discontinued
0.7374	Intermediate Similarity	NPD4334	Discontinued
0.7371	Intermediate Similarity	NPD5899	Approved
0.7371	Intermediate Similarity	NPD5897	Approved
0.7371	Intermediate Similarity	NPD5898	Approved
0.7371	Intermediate Similarity	NPD5473	Discontinued
0.7368	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5444	Phase 1
0.7343	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7470	Discontinued
0.733	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4520	Approved
0.7299	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD750	Phase 2
0.729	Intermediate Similarity	NPD5632	Approved
0.7273	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7957	Phase 1
0.726	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7778	Approved
0.7255	Intermediate Similarity	NPD7777	Approved
0.7255	Intermediate Similarity	NPD53	Approved
0.7251	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2565	Phase 2
0.725	Intermediate Similarity	NPD2564	Approved
0.7244	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5482	Discontinued
0.7214	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8115	Approved
0.7212	Intermediate Similarity	NPD8114	Approved
0.7188	Intermediate Similarity	NPD3006	Discontinued
0.7178	Intermediate Similarity	NPD4315	Phase 2
0.7172	Intermediate Similarity	NPD6178	Phase 3
0.7172	Intermediate Similarity	NPD3436	Approved
0.7171	Intermediate Similarity	NPD4397	Phase 1
0.7163	Intermediate Similarity	NPD5487	Phase 1
0.7156	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5293	Phase 2
0.713	Intermediate Similarity	NPD8358	Approved
0.713	Intermediate Similarity	NPD7878	Phase 2
0.7129	Intermediate Similarity	NPD5913	Phase 3
0.7129	Intermediate Similarity	NPD3947	Discontinued
0.7129	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5072	Discontinued
0.7123	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6206	Phase 1
0.712	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD43	Approved
0.7113	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6182	Approved
0.7109	Intermediate Similarity	NPD5658	Approved
0.7092	Intermediate Similarity	NPD6641	Approved
0.7092	Intermediate Similarity	NPD6642	Approved
0.7087	Intermediate Similarity	NPD6261	Phase 3
0.7085	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8325	Phase 3
0.7083	Intermediate Similarity	NPD8326	Phase 3
0.7083	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3435	Discontinued
0.7064	Intermediate Similarity	NPD6242	Discontinued
0.7062	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7455	Approved
0.7056	Intermediate Similarity	NPD7454	Approved
0.7054	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5426	Phase 3
0.703	Intermediate Similarity	NPD1534	Approved
0.7028	Intermediate Similarity	NPD7665	Phase 2
0.7028	Intermediate Similarity	NPD2916	Discontinued
0.7028	Intermediate Similarity	NPD7666	Phase 3
0.7015	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5475	Discontinued
0.7	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8072	Approved
0.6995	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7727	Phase 2
0.6986	Remote Similarity	NPD7817	Phase 1
0.6986	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4948	Discontinued
0.6964	Remote Similarity	NPD4952	Phase 3
0.6964	Remote Similarity	NPD5479	Discontinued
0.6961	Remote Similarity	NPD2336	Approved
0.6951	Remote Similarity	NPD6165	Phase 2
0.6951	Remote Similarity	NPD7730	Approved
0.6951	Remote Similarity	NPD6164	Phase 2
0.6951	Remote Similarity	NPD7731	Approved
0.6947	Remote Similarity	NPD7791	Approved
0.6947	Remote Similarity	NPD7952	Approved
0.6947	Remote Similarity	NPD7950	Approved
0.6947	Remote Similarity	NPD7790	Approved
0.6947	Remote Similarity	NPD7953	Approved
0.6947	Remote Similarity	NPD7789	Approved
0.6947	Remote Similarity	NPD7951	Approved
0.6947	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7234	Approved
0.6946	Remote Similarity	NPD7233	Approved
0.6942	Remote Similarity	NPD7618	Phase 3
0.6942	Remote Similarity	NPD7619	Phase 3
0.6942	Remote Similarity	NPD7944	Discontinued
0.6941	Remote Similarity	NPD7194	Discontinued
0.6941	Remote Similarity	NPD7404	Approved
0.6938	Remote Similarity	NPD5427	Suspended
0.6938	Remote Similarity	NPD484	Approved
0.6937	Remote Similarity	NPD7271	Approved
0.6934	Remote Similarity	NPD3003	Approved
0.6933	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5450	Discontinued
0.6923	Remote Similarity	NPD1325	Approved
0.6923	Remote Similarity	NPD1326	Approved
0.6923	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7946	Pre-registration
0.6919	Remote Similarity	NPD2144	Approved
0.6919	Remote Similarity	NPD2920	Discontinued
0.6916	Remote Similarity	NPD6529	Discontinued
0.6912	Remote Similarity	NPD4897	Phase 2
0.6904	Remote Similarity	NPD5065	Approved
0.69	Remote Similarity	NPD3038	Discontinued
0.6897	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6999	Discontinued
0.6889	Remote Similarity	NPD7824	Approved
0.6887	Remote Similarity	NPD8283	Approved
0.6887	Remote Similarity	NPD8282	Approved
0.6887	Remote Similarity	NPD56	Approved
0.6884	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4076	Approved
0.6884	Remote Similarity	NPD4079	Approved
0.6883	Remote Similarity	NPD6716	Phase 1
0.6881	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6664	Approved
0.6872	Remote Similarity	NPD4373	Phase 2
0.6872	Remote Similarity	NPD8073	Approved
0.6869	Remote Similarity	NPD8399	Phase 1
0.6869	Remote Similarity	NPD8423	Phase 2
0.6866	Remote Similarity	NPD3319	Phase 1
0.6866	Remote Similarity	NPD3318	Approved
0.6866	Remote Similarity	NPD3320	Approved
0.6866	Remote Similarity	NPD5596	Phase 2
0.6862	Remote Similarity	NPD4463	Approved
0.6862	Remote Similarity	NPD3835	Phase 3
0.6862	Remote Similarity	NPD3833	Phase 3
0.6862	Remote Similarity	NPD4462	Approved
0.686	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD7688	Phase 1
0.6857	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7001	Phase 3
0.6853	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5020	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data