NPASS Compound

Structure

CID86906 OpenBabel06191715422D 34 38 0 0 1 0 0 0 0 0999 V2000 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 13 1 0 0 0 0 8 19 2 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 29 1 0 0 0 0 16 21 1 0 0 0 0 16 22 1 0 0 0 0 17 26 1 0 0 0 0 17 27 1 0 0 0 0 18 32 1 0 0 0 0 20 3 1 1 0 0 0 20 24 1 0 0 0 0 20 32 1 0 0 0 0 21 29 1 0 0 0 0 22 31 1 1 0 0 0 23 10 1 6 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 30 1 1 0 0 0 25 30 1 1 0 0 0 26 29 1 1 0 0 0 27 30 1 1 0 0 0 27 34 1 0 0 0 0 28 33 2 0 0 0 0 28 34 1 0 0 0 0 29 4 1 1 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.37
Volume:	516.318
LogP:	5.794
LogD:	4.472
LogS:	-5.196
# Rotatable Bonds:	5
TPSA:	32.78
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.392
Synthetic Accessibility Score:	5.468
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.889
MDCK Permeability:	8.879257620719727e-06
Pgp-inhibitor:	0.991
Pgp-substrate:	0.716
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.147
30% Bioavailability (F30%):	0.075

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.905
Plasma Protein Binding (PPB):	75.0797348022461%
Volume Distribution (VD):	2.272
Pgp-substrate:	21.441171646118164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.977
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.951
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.782

ADMET: Excretion

Clearance (CL):	17.896
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.811
Human Hepatotoxicity (H-HT):	0.478
Drug-inuced Liver Injury (DILI):	0.719
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.827
Skin Sensitization:	0.934
Carcinogencity:	0.36
Eye Corrosion:	0.008
Eye Irritation:	0.016
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC86906

Natural Product ID:	NPC86906
*Common Name:**	WGJLLAVOYXFCTC-BMSXNQCFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WGJLLAVOYXFCTC-BMSXNQCFSA-N
Standard InCHI:	InChI=1S/C30H48N2O2/c1-19(2)8-13-28(33)34-27-17-26-23(25-12-11-24-20(3)32(7)18-30(24,25)27)10-9-21-16-22(31(5)6)14-15-29(21,26)4/h8-9,20,22-27H,10-18H2,1-7H3/t20-,22-,23-,24+,25-,26-,27+,29-,30+/m0/s1
SMILES:	CC(=CCC(=O)O[C@@H]1C[C@H]2[C@@H](CC=C3C[C@H](CC[C@]23C)N(C)C)[C@@H]2CC[C@@H]3[C@H](C)N(C)C[C@]123)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL364090
PubChem CID:	11225162
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002731] Conanine-type 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
NPO4862	Westiellopsis prolifica	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1602299]
NPO11532	Bidens parviflora	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16880667]
NPO14386	Piper hostmannianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6627	Pinus bungeana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26605	Funtumia elastica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26605	Funtumia elastica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10366	Vincetoxicum stauntonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6627	Pinus bungeana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11532	Bidens parviflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10561	Mentha suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10366	Vincetoxicum stauntonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1421	Papaver hybrid	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3577	Bambusa tulda	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8641	Haemanthus tigrinus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10366	Vincetoxicum stauntonii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6627	Pinus bungeana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11334	Rubus moluccanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14386	Piper hostmannianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10561	Mentha suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14583	Elsholtzia stauntonii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26674	Leucas volkensii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13993	Dimelaena thysanota	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10834	Protea compacta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11532	Bidens parviflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24703	Prostanthera prunelloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12589	Heliotropium angiospermum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5175	Diplospora dubia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO805	Myrmicaria opaciventris	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11073	Alpinia formosana	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13117	Asparagus setaceus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14603	Flindersia australis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9025	Croton balsamifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4862	Westiellopsis prolifica	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26044	Melandrium firmum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21147	Anisocycla grandidieri	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13898	Typhonium flagelliforme	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26605	Funtumia elastica	Species	Apocynaceae	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	2
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	1130.0	nM	PMID[481390]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5130.0	nM	PMID[481390]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Selectivity index	=	4.5	uM	PMID[481390]

☑ 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 NPC86906 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	100
0.1-0.2	790
0.2-0.3	7234
0.3-0.4	16676
0.4-0.5	9354
0.5-0.6	7077
0.6-0.7	1398
0.7-0.8	56
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.951	High Similarity	NPC79238
0.8505	High Similarity	NPC472313
0.8426	Intermediate Similarity	NPC474459
0.8349	Intermediate Similarity	NPC474452
0.8144	Intermediate Similarity	NPC75810
0.8131	Intermediate Similarity	NPC195841
0.8131	Intermediate Similarity	NPC233256
0.789	Intermediate Similarity	NPC46981
0.787	Intermediate Similarity	NPC119329
0.7838	Intermediate Similarity	NPC63511
0.783	Intermediate Similarity	NPC128698
0.783	Intermediate Similarity	NPC239768
0.7767	Intermediate Similarity	NPC93027
0.7736	Intermediate Similarity	NPC91604
0.7706	Intermediate Similarity	NPC212874
0.7632	Intermediate Similarity	NPC478137
0.7547	Intermediate Similarity	NPC476903
0.7544	Intermediate Similarity	NPC80834
0.7544	Intermediate Similarity	NPC469968
0.7526	Intermediate Similarity	NPC44083
0.7526	Intermediate Similarity	NPC153987
0.7477	Intermediate Similarity	NPC140300
0.7404	Intermediate Similarity	NPC84171
0.7383	Intermediate Similarity	NPC289140
0.7353	Intermediate Similarity	NPC474970
0.735	Intermediate Similarity	NPC470538
0.7321	Intermediate Similarity	NPC36497
0.7311	Intermediate Similarity	NPC35037
0.7297	Intermediate Similarity	NPC241879
0.7281	Intermediate Similarity	NPC253645
0.7281	Intermediate Similarity	NPC147835
0.7281	Intermediate Similarity	NPC85001
0.7281	Intermediate Similarity	NPC95920
0.7264	Intermediate Similarity	NPC470224
0.7258	Intermediate Similarity	NPC478136
0.7232	Intermediate Similarity	NPC475239
0.7228	Intermediate Similarity	NPC139206
0.7216	Intermediate Similarity	NPC7214
0.7207	Intermediate Similarity	NPC471083
0.7207	Intermediate Similarity	NPC50815
0.7207	Intermediate Similarity	NPC176012
0.7203	Intermediate Similarity	NPC304646
0.7203	Intermediate Similarity	NPC28280
0.719	Intermediate Similarity	NPC476504
0.719	Intermediate Similarity	NPC242692
0.7184	Intermediate Similarity	NPC264127
0.7156	Intermediate Similarity	NPC474164
0.7131	Intermediate Similarity	NPC472458
0.7129	Intermediate Similarity	NPC215474
0.7115	Intermediate Similarity	NPC478104
0.7105	Intermediate Similarity	NPC25340
0.7087	Intermediate Similarity	NPC470223
0.7075	Intermediate Similarity	NPC471896
0.7054	Intermediate Similarity	NPC247060
0.7049	Intermediate Similarity	NPC470277
0.7048	Intermediate Similarity	NPC28227
0.7048	Intermediate Similarity	NPC97884
0.7048	Intermediate Similarity	NPC472220
0.7043	Intermediate Similarity	NPC159367
0.704	Intermediate Similarity	NPC317654
0.704	Intermediate Similarity	NPC96010
0.7027	Intermediate Similarity	NPC275686
0.7019	Intermediate Similarity	NPC286153
0.7016	Intermediate Similarity	NPC476503
0.7009	Intermediate Similarity	NPC26888
0.6992	Remote Similarity	NPC478138
0.6991	Remote Similarity	NPC474583
0.699	Remote Similarity	NPC100391
0.6975	Remote Similarity	NPC135431
0.6972	Remote Similarity	NPC272732
0.6972	Remote Similarity	NPC311164
0.6964	Remote Similarity	NPC474348
0.6952	Remote Similarity	NPC474684
0.6952	Remote Similarity	NPC142361
0.6949	Remote Similarity	NPC56796
0.6944	Remote Similarity	NPC38232
0.6944	Remote Similarity	NPC473678
0.6923	Remote Similarity	NPC72753
0.6917	Remote Similarity	NPC165396
0.6917	Remote Similarity	NPC209252
0.6916	Remote Similarity	NPC148414
0.6916	Remote Similarity	NPC175628
0.6916	Remote Similarity	NPC111585
0.6909	Remote Similarity	NPC307164
0.6893	Remote Similarity	NPC132386
0.6887	Remote Similarity	NPC470613
0.6887	Remote Similarity	NPC470612
0.6875	Remote Similarity	NPC135799
0.687	Remote Similarity	NPC55462
0.6864	Remote Similarity	NPC66862
0.6863	Remote Similarity	NPC152039
0.6863	Remote Similarity	NPC118329
0.6863	Remote Similarity	NPC142163
0.6863	Remote Similarity	NPC108476
0.6863	Remote Similarity	NPC290495
0.6863	Remote Similarity	NPC195334
0.6857	Remote Similarity	NPC155011
0.6852	Remote Similarity	NPC177641
0.6847	Remote Similarity	NPC292133
0.6842	Remote Similarity	NPC36688
0.6842	Remote Similarity	NPC90538
0.6832	Remote Similarity	NPC305835
0.6832	Remote Similarity	NPC47808
0.6827	Remote Similarity	NPC96055
0.6825	Remote Similarity	NPC48886
0.6825	Remote Similarity	NPC237286
0.6825	Remote Similarity	NPC94881
0.6825	Remote Similarity	NPC265275
0.6822	Remote Similarity	NPC472240
0.6822	Remote Similarity	NPC177141
0.6822	Remote Similarity	NPC474704
0.6822	Remote Similarity	NPC473647
0.6822	Remote Similarity	NPC262858
0.6822	Remote Similarity	NPC475921
0.6822	Remote Similarity	NPC146554
0.6822	Remote Similarity	NPC474889
0.681	Remote Similarity	NPC169375
0.6807	Remote Similarity	NPC477291
0.6807	Remote Similarity	NPC476498
0.6804	Remote Similarity	NPC21773
0.6803	Remote Similarity	NPC470276
0.6796	Remote Similarity	NPC286786
0.6792	Remote Similarity	NPC187376
0.6792	Remote Similarity	NPC159046
0.6792	Remote Similarity	NPC233836
0.6792	Remote Similarity	NPC167877
0.6786	Remote Similarity	NPC252295
0.678	Remote Similarity	NPC472359
0.678	Remote Similarity	NPC287764
0.6772	Remote Similarity	NPC280903
0.6765	Remote Similarity	NPC304194
0.6765	Remote Similarity	NPC206735
0.6765	Remote Similarity	NPC269791
0.6759	Remote Similarity	NPC273199
0.6757	Remote Similarity	NPC54248
0.6757	Remote Similarity	NPC475178
0.6757	Remote Similarity	NPC304899
0.6757	Remote Similarity	NPC253115
0.6757	Remote Similarity	NPC276103
0.6731	Remote Similarity	NPC171639
0.6729	Remote Similarity	NPC242864
0.6729	Remote Similarity	NPC473879
0.6729	Remote Similarity	NPC474845
0.6727	Remote Similarity	NPC280710
0.6727	Remote Similarity	NPC474922
0.6727	Remote Similarity	NPC243985
0.6727	Remote Similarity	NPC159410
0.6726	Remote Similarity	NPC470906
0.6726	Remote Similarity	NPC476303
0.6699	Remote Similarity	NPC329782
0.6698	Remote Similarity	NPC470051
0.6698	Remote Similarity	NPC195640
0.6698	Remote Similarity	NPC470050
0.6698	Remote Similarity	NPC10005
0.6698	Remote Similarity	NPC9892
0.6698	Remote Similarity	NPC91525
0.6698	Remote Similarity	NPC28252
0.6698	Remote Similarity	NPC325594
0.6698	Remote Similarity	NPC55309
0.6698	Remote Similarity	NPC329943
0.6697	Remote Similarity	NPC49420
0.6697	Remote Similarity	NPC189520
0.6697	Remote Similarity	NPC234335
0.6696	Remote Similarity	NPC98765
0.6696	Remote Similarity	NPC36321
0.6696	Remote Similarity	NPC141401
0.6696	Remote Similarity	NPC240650
0.6696	Remote Similarity	NPC23680
0.6696	Remote Similarity	NPC475033
0.6696	Remote Similarity	NPC475032
0.6694	Remote Similarity	NPC476499
0.6694	Remote Similarity	NPC470540
0.6667	Remote Similarity	NPC279974
0.6667	Remote Similarity	NPC77168
0.6667	Remote Similarity	NPC100906
0.6667	Remote Similarity	NPC476904
0.6667	Remote Similarity	NPC124358
0.6667	Remote Similarity	NPC139566
0.6667	Remote Similarity	NPC128496
0.6667	Remote Similarity	NPC469599
0.6667	Remote Similarity	NPC475509
0.6667	Remote Similarity	NPC102414
0.6667	Remote Similarity	NPC118275
0.6667	Remote Similarity	NPC84271
0.6641	Remote Similarity	NPC470537
0.6638	Remote Similarity	NPC472228
0.6638	Remote Similarity	NPC471293
0.6638	Remote Similarity	NPC472227
0.6636	Remote Similarity	NPC170220
0.6636	Remote Similarity	NPC79117
0.6636	Remote Similarity	NPC162107
0.6636	Remote Similarity	NPC470375
0.6636	Remote Similarity	NPC474436
0.6636	Remote Similarity	NPC49776
0.6636	Remote Similarity	NPC63118
0.6636	Remote Similarity	NPC107674
0.6636	Remote Similarity	NPC474185
0.6636	Remote Similarity	NPC141497
0.6636	Remote Similarity	NPC46912
0.6636	Remote Similarity	NPC470376

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 NPC86906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	484
0.2-0.3	2972
0.3-0.4	4016
0.4-0.5	1100
0.5-0.6	374
0.6-0.7	111
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7547	Intermediate Similarity	NPD5349	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7336	Phase 2
0.6949	Remote Similarity	NPD7335	Phase 2
0.6949	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7755	Approved
0.6917	Remote Similarity	NPD7754	Approved
0.6807	Remote Similarity	NPD8077	Approved
0.6807	Remote Similarity	NPD8078	Approved
0.6789	Remote Similarity	NPD6399	Phase 3
0.6774	Remote Similarity	NPD6908	Approved
0.6774	Remote Similarity	NPD6909	Approved
0.6729	Remote Similarity	NPD6903	Approved
0.6698	Remote Similarity	NPD6409	Approved
0.6698	Remote Similarity	NPD7334	Approved
0.6698	Remote Similarity	NPD7146	Approved
0.6698	Remote Similarity	NPD5330	Approved
0.6698	Remote Similarity	NPD6684	Approved
0.6698	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6008	Approved
0.6574	Remote Similarity	NPD6672	Approved
0.6574	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5737	Approved
0.6514	Remote Similarity	NPD6051	Approved
0.6509	Remote Similarity	NPD4786	Approved
0.6486	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7519	Approved
0.648	Remote Similarity	NPD7517	Approved
0.648	Remote Similarity	NPD7518	Approved
0.6441	Remote Similarity	NPD8040	Discontinued
0.6436	Remote Similarity	NPD7339	Approved
0.6436	Remote Similarity	NPD6942	Approved
0.6429	Remote Similarity	NPD6001	Approved
0.641	Remote Similarity	NPD7911	Approved
0.641	Remote Similarity	NPD7986	Approved
0.641	Remote Similarity	NPD7987	Approved
0.641	Remote Similarity	NPD7912	Approved
0.6389	Remote Similarity	NPD6098	Approved
0.6389	Remote Similarity	NPD8308	Discontinued
0.6364	Remote Similarity	NPD5328	Approved
0.6348	Remote Similarity	NPD7638	Approved
0.6333	Remote Similarity	NPD7320	Approved
0.6321	Remote Similarity	NPD3667	Approved
0.6303	Remote Similarity	NPD6402	Approved
0.6303	Remote Similarity	NPD5739	Approved
0.6303	Remote Similarity	NPD7333	Discontinued
0.6303	Remote Similarity	NPD6675	Approved
0.6303	Remote Similarity	NPD7128	Approved
0.6296	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7639	Approved
0.6293	Remote Similarity	NPD7640	Approved
0.6286	Remote Similarity	NPD7525	Registered
0.6283	Remote Similarity	NPD5707	Approved
0.6283	Remote Similarity	NPD7900	Approved
0.6283	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7748	Approved
0.6279	Remote Similarity	NPD7122	Discontinued
0.6269	Remote Similarity	NPD8449	Approved
0.625	Remote Similarity	NPD7989	Approved
0.625	Remote Similarity	NPD6079	Approved
0.625	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7990	Approved
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD8034	Phase 2
0.6239	Remote Similarity	NPD3618	Phase 1
0.6222	Remote Similarity	NPD8450	Suspended
0.6216	Remote Similarity	NPD6080	Approved
0.6216	Remote Similarity	NPD6673	Approved
0.6216	Remote Similarity	NPD6904	Approved
0.6214	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD8336	Approved
0.6212	Remote Similarity	NPD8337	Approved
0.621	Remote Similarity	NPD8298	Phase 2
0.6204	Remote Similarity	NPD3668	Phase 3
0.6198	Remote Similarity	NPD6881	Approved
0.6198	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD5207	Approved
0.6154	Remote Similarity	NPD8144	Approved
0.6154	Remote Similarity	NPD8143	Approved
0.6148	Remote Similarity	NPD6373	Approved
0.6148	Remote Similarity	NPD8338	Approved
0.6148	Remote Similarity	NPD6845	Suspended
0.6148	Remote Similarity	NPD6372	Approved
0.6126	Remote Similarity	NPD5208	Approved
0.6121	Remote Similarity	NPD6083	Phase 2
0.6121	Remote Similarity	NPD6084	Phase 2
0.6121	Remote Similarity	NPD7902	Approved
0.6116	Remote Similarity	NPD5697	Approved
0.6116	Remote Similarity	NPD5706	Approved
0.6116	Remote Similarity	NPD5704	Approved
0.6116	Remote Similarity	NPD5705	Approved
0.6116	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD4766	Approved
0.6106	Remote Similarity	NPD7515	Phase 2
0.6098	Remote Similarity	NPD6420	Discontinued
0.6098	Remote Similarity	NPD7102	Approved
0.6098	Remote Similarity	NPD7290	Approved
0.6098	Remote Similarity	NPD6883	Approved
0.6066	Remote Similarity	NPD6011	Approved
0.6053	Remote Similarity	NPD4202	Approved
0.6048	Remote Similarity	NPD6649	Approved
0.6048	Remote Similarity	NPD6869	Approved
0.6048	Remote Similarity	NPD6847	Approved
0.6048	Remote Similarity	NPD6650	Approved
0.6048	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6617	Approved
0.6048	Remote Similarity	NPD8130	Phase 1
0.6043	Remote Similarity	NPD6334	Approved
0.6043	Remote Similarity	NPD6333	Approved
0.6038	Remote Similarity	NPD7645	Phase 2
0.6036	Remote Similarity	NPD3573	Approved
0.6033	Remote Similarity	NPD6920	Discontinued
0.6017	Remote Similarity	NPD8418	Phase 2
0.6016	Remote Similarity	NPD6014	Approved
0.6016	Remote Similarity	NPD6012	Approved
0.6016	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD5771	Approved
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD8297	Approved
0.5965	Remote Similarity	NPD6050	Approved
0.5965	Remote Similarity	NPD5693	Phase 1
0.5948	Remote Similarity	NPD5695	Phase 3
0.5948	Remote Similarity	NPD7991	Discontinued
0.5941	Remote Similarity	NPD2694	Approved
0.5941	Remote Similarity	NPD2697	Approved
0.5941	Remote Similarity	NPD2696	Approved
0.5941	Remote Similarity	NPD2695	Approved
0.5938	Remote Similarity	NPD7115	Discovery
0.5935	Remote Similarity	NPD6415	Discontinued
0.5932	Remote Similarity	NPD4225	Approved
0.5932	Remote Similarity	NPD5696	Approved
0.5909	Remote Similarity	NPD3665	Phase 1
0.5909	Remote Similarity	NPD3133	Approved
0.5909	Remote Similarity	NPD7604	Phase 2
0.5909	Remote Similarity	NPD3666	Approved
0.5897	Remote Similarity	NPD4697	Phase 3
0.5897	Remote Similarity	NPD5222	Approved
0.5897	Remote Similarity	NPD5221	Approved
0.5897	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6404	Discontinued
0.5877	Remote Similarity	NPD5692	Phase 3
0.5868	Remote Similarity	NPD6052	Approved
0.5865	Remote Similarity	NPD4784	Approved
0.5865	Remote Similarity	NPD4785	Approved
0.5865	Remote Similarity	NPD6926	Approved
0.5865	Remote Similarity	NPD6924	Approved
0.5859	Remote Similarity	NPD6868	Approved
0.5856	Remote Similarity	NPD1694	Approved
0.5847	Remote Similarity	NPD5173	Approved
0.5847	Remote Similarity	NPD7919	Phase 3
0.5847	Remote Similarity	NPD4755	Approved
0.5847	Remote Similarity	NPD7920	Phase 3
0.5839	Remote Similarity	NPD7260	Phase 2
0.5826	Remote Similarity	NPD5694	Approved
0.5826	Remote Similarity	NPD7637	Suspended
0.5825	Remote Similarity	NPD4243	Approved
0.5798	Remote Similarity	NPD8088	Phase 1
0.5785	Remote Similarity	NPD7632	Discontinued
0.5769	Remote Similarity	NPD6335	Approved
0.5766	Remote Similarity	NPD7751	Phase 1
0.5758	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6933	Approved
0.5752	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.575	Remote Similarity	NPD5286	Approved
0.575	Remote Similarity	NPD5285	Approved
0.575	Remote Similarity	NPD4696	Approved
0.575	Remote Similarity	NPD4700	Approved
0.5746	Remote Similarity	NPD2608	Approved
0.5746	Remote Similarity	NPD4215	Approved
0.5746	Remote Similarity	NPD4217	Approved
0.5746	Remote Similarity	NPD3132	Approved
0.5746	Remote Similarity	NPD2610	Approved
0.5746	Remote Similarity	NPD2611	Approved
0.5746	Remote Similarity	NPD4216	Approved
0.5746	Remote Similarity	NPD2612	Approved
0.5746	Remote Similarity	NPD3131	Approved
0.5746	Remote Similarity	NPD2609	Approved
0.5746	Remote Similarity	NPD7492	Approved
0.5746	Remote Similarity	NPD4218	Approved
0.5741	Remote Similarity	NPD4195	Approved
0.5736	Remote Similarity	NPD6274	Approved
0.5727	Remote Similarity	NPD4223	Phase 3
0.5727	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD4221	Approved
0.5726	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD7101	Approved
0.5725	Remote Similarity	NPD7100	Approved
0.5714	Remote Similarity	NPD5329	Approved
0.5704	Remote Similarity	NPD6616	Approved
0.5703	Remote Similarity	NPD4632	Approved
0.5703	Remote Similarity	NPD2607	Approved
0.5702	Remote Similarity	NPD5223	Approved
0.5692	Remote Similarity	NPD6317	Approved
0.569	Remote Similarity	NPD6411	Approved
0.5688	Remote Similarity	NPD4748	Discontinued
0.5682	Remote Similarity	NPD6054	Approved
0.5682	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD6059	Approved
0.5682	Remote Similarity	NPD7147	Phase 3
0.5676	Remote Similarity	NPD6695	Phase 3

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