NPASS Compound

Structure

CID190332 OpenBabel06191715572D 21 25 0 0 1 0 0 0 0 0999 V2000 1.5153 0.8749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7576 -0.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7575 2.1875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2735 -0.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2733 1.3126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7580 -0.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3777 0.4378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7577 1.3124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5156 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5155 0.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.6250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0312 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 0.8752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7580 1.3123 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.8749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7579 2.1874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.0002 3.5278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5397 2.6388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8635 -0.2702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8633 1.1457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 8 1 0 0 0 0 2 17 1 0 0 0 0 3 8 2 0 0 0 0 3 11 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 7 21 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 6 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 10 1 6 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 1 0 0 0 16 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	287.12
Volume:	278.122
LogP:	0.981
LogD:	1.096
LogS:	-1.831
# Rotatable Bonds:	0
TPSA:	62.16
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	4.165
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.77
MDCK Permeability:	2.4716950065339915e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.58
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	74.39615631103516%
Volume Distribution (VD):	2.44
Pgp-substrate:	22.770721435546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.703
CYP1A2-substrate:	0.562
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.389
CYP2D6-inhibitor:	0.932
CYP2D6-substrate:	0.656
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.345

ADMET: Excretion

Clearance (CL):	12.885
Half-life (T1/2):	0.599

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.113
AMES Toxicity:	0.201
Rat Oral Acute Toxicity:	0.81
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.052
Carcinogencity:	0.91
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC190332

Natural Product ID:	NPC190332
*Common Name:**	XGVJWXAYKUHDOO-MSQAHXEGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XGVJWXAYKUHDOO-MSQAHXEGSA-N
Standard InCHI:	InChI=1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14+,15-,16-/m1/s1
SMILES:	O[C@@H]1C=C2CCN3[C@H]2[C@@H]([C@@H]1O)c1cc2OCOc2cc1C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL583716
PubChem CID:	12305849
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004120] Lycorine-type amaryllidaceae 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
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ja01076a047]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10846753]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15595606]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20524638]
NPO27062	Narcissus pseudonarcissus	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[21105682]
NPO9927.2	Crinum asiaticum var. sinicum	Varieties	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21314165]
NPO9927.2	Crinum asiaticum var. sinicum	Varieties	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[21314165]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510636]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	whole plants	n.a.	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2348199]
NPO16709	Clivia miniata	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24221429]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26913788]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6512532]
NPO16709	Clivia miniata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7153775]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22747	Lycoris sanguinea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1598	Leucojum vernum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9942.1	Narcissus tazetta var. chinensis	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16709	Clivia miniata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27062	Narcissus pseudonarcissus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927.2	Crinum asiaticum var. sinicum	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927.1	Crinum asiaticum var. japonicum	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16709	Clivia miniata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27062	Narcissus pseudonarcissus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25221	Crinum macowanii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22747	Lycoris sanguinea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927.1	Crinum asiaticum var. japonicum	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9942.1	Narcissus tazetta var. chinensis	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927.2	Crinum asiaticum var. sinicum	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1598	Leucojum vernum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1598	Leucojum vernum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16709	Clivia miniata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27062	Narcissus pseudonarcissus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25221	Crinum macowanii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22747	Lycoris sanguinea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	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	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[572693]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10000.0	nM	PMID[572693]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[572693]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[572693]

☑ 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 NPC190332 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	301
0.1-0.2	1259
0.2-0.3	4347
0.3-0.4	12240
0.4-0.5	7655
0.5-0.6	12200
0.6-0.7	3657
0.7-0.8	773
0.8-0.85	169
0.85-0.9	43
0.9-0.95	42
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC181653
0.9805	High Similarity	NPC320104
0.9744	High Similarity	NPC100566
0.9625	High Similarity	NPC237044
0.9565	High Similarity	NPC474325
0.9563	High Similarity	NPC304675
0.9506	High Similarity	NPC474745
0.9434	High Similarity	NPC58766
0.9434	High Similarity	NPC475686
0.9375	High Similarity	NPC474475
0.9375	High Similarity	NPC311991
0.9333	High Similarity	NPC475981
0.9333	High Similarity	NPC474746
0.9317	High Similarity	NPC477640
0.9317	High Similarity	NPC470739
0.9317	High Similarity	NPC225597
0.9313	High Similarity	NPC82533
0.9313	High Similarity	NPC290759
0.9313	High Similarity	NPC266176
0.9313	High Similarity	NPC158148
0.9299	High Similarity	NPC205167
0.9299	High Similarity	NPC215829
0.9299	High Similarity	NPC97072
0.9299	High Similarity	NPC249274
0.925	High Similarity	NPC57812
0.925	High Similarity	NPC474324
0.9222	High Similarity	NPC230098
0.9202	High Similarity	NPC187678
0.9193	High Similarity	NPC475845
0.9187	High Similarity	NPC476002
0.9177	High Similarity	NPC4304
0.9136	High Similarity	NPC474708
0.9091	High Similarity	NPC294790
0.9091	High Similarity	NPC15919
0.9091	High Similarity	NPC148693
0.9091	High Similarity	NPC118633
0.903	High Similarity	NPC474470
0.8924	High Similarity	NPC78733
0.8922	High Similarity	NPC244554
0.8817	High Similarity	NPC275132
0.8795	High Similarity	NPC2314
0.8788	High Similarity	NPC75958
0.878	High Similarity	NPC252960
0.8773	High Similarity	NPC247972
0.875	High Similarity	NPC147091
0.8735	High Similarity	NPC65403
0.8713	High Similarity	NPC9867
0.8712	High Similarity	NPC218614
0.8679	High Similarity	NPC223124
0.8679	High Similarity	NPC148898
0.8642	High Similarity	NPC59028
0.8642	High Similarity	NPC92191
0.8642	High Similarity	NPC111485
0.8631	High Similarity	NPC199465
0.8631	High Similarity	NPC229166
0.8631	High Similarity	NPC128560
0.8631	High Similarity	NPC49353
0.8596	High Similarity	NPC248642
0.8588	High Similarity	NPC126284
0.8562	High Similarity	NPC233029
0.8562	High Similarity	NPC210148
0.8554	High Similarity	NPC210918
0.8553	High Similarity	NPC274026
0.8553	High Similarity	NPC223125
0.8547	High Similarity	NPC156576
0.8545	High Similarity	NPC238530
0.8545	High Similarity	NPC232514
0.8545	High Similarity	NPC276944
0.8545	High Similarity	NPC180306
0.8544	High Similarity	NPC475959
0.8529	High Similarity	NPC320223
0.8529	High Similarity	NPC114364
0.8519	High Similarity	NPC234392
0.8519	High Similarity	NPC31311
0.8476	Intermediate Similarity	NPC165797
0.8475	Intermediate Similarity	NPC33256
0.8447	Intermediate Similarity	NPC82285
0.8447	Intermediate Similarity	NPC133011
0.8443	Intermediate Similarity	NPC150879
0.8443	Intermediate Similarity	NPC301189
0.8443	Intermediate Similarity	NPC298186
0.8434	Intermediate Similarity	NPC302527
0.8434	Intermediate Similarity	NPC167546
0.8434	Intermediate Similarity	NPC16805
0.8415	Intermediate Similarity	NPC477080
0.8405	Intermediate Similarity	NPC146288
0.8383	Intermediate Similarity	NPC24264
0.8383	Intermediate Similarity	NPC476432
0.8382	Intermediate Similarity	NPC233718
0.8382	Intermediate Similarity	NPC116284
0.8363	Intermediate Similarity	NPC283999
0.8344	Intermediate Similarity	NPC216459
0.8344	Intermediate Similarity	NPC41178
0.8344	Intermediate Similarity	NPC138487
0.8343	Intermediate Similarity	NPC214116
0.8333	Intermediate Similarity	NPC298979
0.8333	Intermediate Similarity	NPC247389
0.8324	Intermediate Similarity	NPC477561
0.8324	Intermediate Similarity	NPC476574
0.8324	Intermediate Similarity	NPC155442
0.8324	Intermediate Similarity	NPC312918
0.8323	Intermediate Similarity	NPC225774
0.8323	Intermediate Similarity	NPC231198
0.8313	Intermediate Similarity	NPC246587
0.8313	Intermediate Similarity	NPC428
0.8313	Intermediate Similarity	NPC147390
0.8313	Intermediate Similarity	NPC24233
0.8313	Intermediate Similarity	NPC135538
0.8313	Intermediate Similarity	NPC476571
0.8303	Intermediate Similarity	NPC69360
0.8294	Intermediate Similarity	NPC57272
0.8276	Intermediate Similarity	NPC476575
0.8274	Intermediate Similarity	NPC219341
0.8266	Intermediate Similarity	NPC99179
0.8263	Intermediate Similarity	NPC233650
0.825	Intermediate Similarity	NPC179825
0.825	Intermediate Similarity	NPC191376
0.825	Intermediate Similarity	NPC321505
0.8239	Intermediate Similarity	NPC130926
0.8239	Intermediate Similarity	NPC185838
0.8229	Intermediate Similarity	NPC135772
0.8225	Intermediate Similarity	NPC210140
0.8214	Intermediate Similarity	NPC196447
0.8214	Intermediate Similarity	NPC306843
0.8214	Intermediate Similarity	NPC212794
0.8214	Intermediate Similarity	NPC96603
0.8214	Intermediate Similarity	NPC13504
0.8214	Intermediate Similarity	NPC136508
0.8214	Intermediate Similarity	NPC78222
0.8214	Intermediate Similarity	NPC477563
0.8214	Intermediate Similarity	NPC134858
0.8214	Intermediate Similarity	NPC253043
0.821	Intermediate Similarity	NPC97221
0.821	Intermediate Similarity	NPC151895
0.821	Intermediate Similarity	NPC192768
0.821	Intermediate Similarity	NPC220858
0.821	Intermediate Similarity	NPC88249
0.8198	Intermediate Similarity	NPC477558
0.8194	Intermediate Similarity	NPC7018
0.8187	Intermediate Similarity	NPC19520
0.8187	Intermediate Similarity	NPC149090
0.8166	Intermediate Similarity	NPC124657
0.8155	Intermediate Similarity	NPC324144
0.8155	Intermediate Similarity	NPC59567
0.8148	Intermediate Similarity	NPC477565
0.8148	Intermediate Similarity	NPC103379
0.8146	Intermediate Similarity	NPC82763
0.8144	Intermediate Similarity	NPC477559
0.8144	Intermediate Similarity	NPC232924
0.8144	Intermediate Similarity	NPC160298
0.8144	Intermediate Similarity	NPC306902
0.8144	Intermediate Similarity	NPC266753
0.8137	Intermediate Similarity	NPC476151
0.8133	Intermediate Similarity	NPC475326
0.8129	Intermediate Similarity	NPC6152
0.8121	Intermediate Similarity	NPC76079
0.8121	Intermediate Similarity	NPC249797
0.8121	Intermediate Similarity	NPC278799
0.8121	Intermediate Similarity	NPC5238
0.8121	Intermediate Similarity	NPC110416
0.8121	Intermediate Similarity	NPC295691
0.8121	Intermediate Similarity	NPC469817
0.8121	Intermediate Similarity	NPC193949
0.8121	Intermediate Similarity	NPC54379
0.8121	Intermediate Similarity	NPC39701
0.8121	Intermediate Similarity	NPC207757
0.8121	Intermediate Similarity	NPC172765
0.8121	Intermediate Similarity	NPC127674
0.8121	Intermediate Similarity	NPC184026
0.8121	Intermediate Similarity	NPC189266
0.8121	Intermediate Similarity	NPC276588
0.8121	Intermediate Similarity	NPC204828
0.8121	Intermediate Similarity	NPC2413
0.8118	Intermediate Similarity	NPC158376
0.8118	Intermediate Similarity	NPC12053
0.8118	Intermediate Similarity	NPC117188
0.8118	Intermediate Similarity	NPC205421
0.8118	Intermediate Similarity	NPC306555
0.8118	Intermediate Similarity	NPC145832
0.8118	Intermediate Similarity	NPC474931
0.8118	Intermediate Similarity	NPC81218
0.8107	Intermediate Similarity	NPC24465
0.8101	Intermediate Similarity	NPC188163
0.8101	Intermediate Similarity	NPC213206
0.8101	Intermediate Similarity	NPC328750
0.8101	Intermediate Similarity	NPC474915
0.809	Intermediate Similarity	NPC186546
0.809	Intermediate Similarity	NPC476576
0.8086	Intermediate Similarity	NPC37144
0.8086	Intermediate Similarity	NPC59907
0.8072	Intermediate Similarity	NPC186063
0.807	Intermediate Similarity	NPC160570
0.8068	Intermediate Similarity	NPC102760
0.8065	Intermediate Similarity	NPC80472
0.8059	Intermediate Similarity	NPC13916
0.8059	Intermediate Similarity	NPC264850
0.8057	Intermediate Similarity	NPC32154
0.8056	Intermediate Similarity	NPC117717
0.8046	Intermediate Similarity	NPC241704
0.8038	Intermediate Similarity	NPC314682

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 NPC190332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	634
0.2-0.3	950
0.3-0.4	2385
0.4-0.5	2680
0.5-0.6	1636
0.6-0.7	567
0.7-0.8	112
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD2970	Approved
0.8333	Intermediate Similarity	NPD2969	Approved
0.8282	Intermediate Similarity	NPD4773	Phase 2
0.8282	Intermediate Similarity	NPD4772	Phase 2
0.8176	Intermediate Similarity	NPD2489	Approved
0.8176	Intermediate Similarity	NPD27	Approved
0.8166	Intermediate Similarity	NPD3051	Approved
0.8101	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD6071	Discontinued
0.8024	Intermediate Similarity	NPD2563	Approved
0.8024	Intermediate Similarity	NPD2560	Approved
0.7914	Intermediate Similarity	NPD4584	Approved
0.7861	Intermediate Similarity	NPD4481	Phase 3
0.7857	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2977	Approved
0.7857	Intermediate Similarity	NPD2978	Approved
0.7809	Intermediate Similarity	NPD7311	Approved
0.7809	Intermediate Similarity	NPD7313	Approved
0.7809	Intermediate Similarity	NPD7312	Approved
0.7809	Intermediate Similarity	NPD7310	Approved
0.7778	Intermediate Similarity	NPD4663	Approved
0.7765	Intermediate Similarity	NPD7309	Approved
0.7759	Intermediate Similarity	NPD2898	Approved
0.773	Intermediate Similarity	NPD5241	Discontinued
0.7716	Intermediate Similarity	NPD4237	Approved
0.7716	Intermediate Similarity	NPD4236	Phase 3
0.7711	Intermediate Similarity	NPD3639	Approved
0.7711	Intermediate Similarity	NPD3641	Approved
0.7711	Intermediate Similarity	NPD3640	Phase 3
0.7709	Intermediate Similarity	NPD7280	Phase 3
0.7709	Intermediate Similarity	NPD7281	Phase 3
0.7709	Intermediate Similarity	NPD4578	Approved
0.7709	Intermediate Similarity	NPD4577	Approved
0.7705	Intermediate Similarity	NPD7296	Approved
0.7688	Intermediate Similarity	NPD6107	Approved
0.7683	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD5582	Discontinued
0.7647	Intermediate Similarity	NPD5772	Approved
0.7647	Intermediate Similarity	NPD5773	Approved
0.7644	Intermediate Similarity	NPD4010	Discontinued
0.7637	Intermediate Similarity	NPD7906	Approved
0.7616	Intermediate Similarity	NPD5604	Discontinued
0.7594	Intermediate Similarity	NPD4420	Approved
0.7588	Intermediate Similarity	NPD7298	Approved
0.7569	Intermediate Similarity	NPD8053	Approved
0.7569	Intermediate Similarity	NPD8054	Approved
0.7569	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5006	Approved
0.7526	Intermediate Similarity	NPD5005	Approved
0.7515	Intermediate Similarity	NPD4017	Approved
0.7514	Intermediate Similarity	NPD7831	Phase 2
0.7514	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7833	Phase 2
0.7485	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4210	Discontinued
0.7446	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4166	Phase 2
0.743	Intermediate Similarity	NPD5312	Approved
0.743	Intermediate Similarity	NPD8156	Discontinued
0.743	Intermediate Similarity	NPD5313	Approved
0.7429	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6031	Approved
0.7396	Intermediate Similarity	NPD6030	Approved
0.7374	Intermediate Similarity	NPD8099	Discontinued
0.7374	Intermediate Similarity	NPD8251	Approved
0.7374	Intermediate Similarity	NPD8252	Approved
0.7366	Intermediate Similarity	NPD2488	Approved
0.7366	Intermediate Similarity	NPD2490	Approved
0.736	Intermediate Similarity	NPD7827	Phase 1
0.7289	Intermediate Similarity	NPD5177	Phase 3
0.7289	Intermediate Similarity	NPD3060	Approved
0.7277	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6788	Approved
0.7228	Intermediate Similarity	NPD2968	Approved
0.7228	Intermediate Similarity	NPD2971	Approved
0.7222	Intermediate Similarity	NPD2238	Phase 2
0.7219	Intermediate Similarity	NPD2421	Approved
0.7219	Intermediate Similarity	NPD2420	Approved
0.7211	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4005	Discontinued
0.7202	Intermediate Similarity	NPD3450	Approved
0.7202	Intermediate Similarity	NPD3452	Approved
0.7193	Intermediate Similarity	NPD4727	Phase 1
0.7165	Intermediate Similarity	NPD3057	Approved
0.716	Intermediate Similarity	NPD3845	Phase 1
0.7158	Intermediate Similarity	NPD6297	Approved
0.7152	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2492	Phase 1
0.7128	Intermediate Similarity	NPD4004	Approved
0.7128	Intermediate Similarity	NPD4002	Approved
0.7122	Intermediate Similarity	NPD6997	Phase 2
0.7118	Intermediate Similarity	NPD3124	Discontinued
0.7113	Intermediate Similarity	NPD2493	Approved
0.7113	Intermediate Similarity	NPD2494	Approved
0.711	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5718	Phase 2
0.7097	Intermediate Similarity	NPD6851	Approved
0.7097	Intermediate Similarity	NPD6853	Approved
0.7093	Intermediate Similarity	NPD2122	Discontinued
0.7092	Intermediate Similarity	NPD4583	Approved
0.7092	Intermediate Similarity	NPD4582	Approved
0.709	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4162	Approved
0.7083	Intermediate Similarity	NPD2974	Approved
0.7083	Intermediate Similarity	NPD2973	Approved
0.7083	Intermediate Similarity	NPD2975	Approved
0.7077	Intermediate Similarity	NPD3533	Approved
0.7077	Intermediate Similarity	NPD2972	Approved
0.7077	Intermediate Similarity	NPD3448	Approved
0.7076	Intermediate Similarity	NPD1424	Approved
0.707	Intermediate Similarity	NPD3705	Approved
0.7066	Intermediate Similarity	NPD1375	Discontinued
0.7062	Intermediate Similarity	NPD4580	Approved
0.7055	Intermediate Similarity	NPD2674	Phase 3
0.7033	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD823	Approved
0.703	Intermediate Similarity	NPD817	Approved
0.7022	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6688	Approved
0.7017	Intermediate Similarity	NPD6687	Approved
0.7012	Intermediate Similarity	NPD3110	Approved
0.7012	Intermediate Similarity	NPD3109	Approved
0.7006	Intermediate Similarity	NPD2161	Phase 2
0.7005	Intermediate Similarity	NPD4040	Phase 1
0.6995	Remote Similarity	NPD7047	Phase 3
0.6994	Remote Similarity	NPD3145	Approved
0.6994	Remote Similarity	NPD3144	Approved
0.699	Remote Similarity	NPD2491	Approved
0.6989	Remote Similarity	NPD3384	Approved
0.6989	Remote Similarity	NPD3383	Approved
0.6989	Remote Similarity	NPD3382	Approved
0.6988	Remote Similarity	NPD6896	Approved
0.6988	Remote Similarity	NPD6895	Approved
0.6977	Remote Similarity	NPD4123	Phase 3
0.6975	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4967	Phase 2
0.6966	Remote Similarity	NPD4965	Approved
0.6966	Remote Similarity	NPD4966	Approved
0.6959	Remote Similarity	NPD6667	Approved
0.6959	Remote Similarity	NPD6666	Approved
0.6959	Remote Similarity	NPD7124	Phase 2
0.6954	Remote Similarity	NPD3686	Approved
0.6954	Remote Similarity	NPD3687	Approved
0.6946	Remote Similarity	NPD1753	Discontinued
0.6946	Remote Similarity	NPD4108	Discontinued
0.6941	Remote Similarity	NPD5754	Discontinued
0.6941	Remote Similarity	NPD6331	Phase 2
0.6936	Remote Similarity	NPD6090	Discontinued
0.6927	Remote Similarity	NPD4055	Discovery
0.6923	Remote Similarity	NPD7037	Approved
0.6923	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5978	Approved
0.691	Remote Similarity	NPD5977	Approved
0.6906	Remote Similarity	NPD7802	Discontinued
0.6901	Remote Similarity	NPD2677	Approved
0.6901	Remote Similarity	NPD5160	Discontinued
0.6901	Remote Similarity	NPD6723	Discontinued
0.69	Remote Similarity	NPD4859	Phase 1
0.6897	Remote Similarity	NPD5976	Discontinued
0.6895	Remote Similarity	NPD6841	Approved
0.6895	Remote Similarity	NPD6842	Approved
0.6895	Remote Similarity	NPD6843	Phase 3
0.6893	Remote Similarity	NPD37	Approved
0.6889	Remote Similarity	NPD6234	Discontinued
0.6888	Remote Similarity	NPD4107	Approved
0.6885	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6674	Discontinued
0.6882	Remote Similarity	NPD7007	Discovery
0.6881	Remote Similarity	NPD5676	Approved
0.6879	Remote Similarity	NPD7020	Approved
0.6879	Remote Similarity	NPD7019	Approved
0.6864	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3656	Approved
0.6851	Remote Similarity	NPD4666	Phase 3
0.6851	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7526	Approved
0.6839	Remote Similarity	NPD52	Approved
0.6839	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2668	Approved
0.6835	Remote Similarity	NPD2667	Approved
0.6828	Remote Similarity	NPD3885	Approved
0.6813	Remote Similarity	NPD2230	Approved
0.6813	Remote Similarity	NPD2232	Approved
0.6813	Remote Similarity	NPD2233	Approved
0.6811	Remote Similarity	NPD7228	Approved
0.681	Remote Similarity	NPD3637	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