NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	359.576
LogP:	2.668
LogD:	2.396
LogS:	-4.048
# Rotatable Bonds:	3
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	5.021
Fsp3:	0.6
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:	-4.92
MDCK Permeability:	1.4106098205957096e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	74.33855438232422%
Volume Distribution (VD):	2.059
Pgp-substrate:	23.24701690673828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.357
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.624
CYP2C19-substrate:	0.562
CYP2C9-inhibitor:	0.373
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.32
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.748
CYP3A4-substrate:	0.377

ADMET: Excretion

Clearance (CL):	6.279
Half-life (T1/2):	0.548

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.836
Drug-inuced Liver Injury (DILI):	0.207
AMES Toxicity:	0.189
Rat Oral Acute Toxicity:	0.826
Maximum Recommended Daily Dose:	0.388
Skin Sensitization:	0.765
Carcinogencity:	0.151
Eye Corrosion:	0.024
Eye Irritation:	0.052
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC477125

Natural Product ID:	NPC477125
*Common Name:**	[(3R,3aR,5aS,6R,9aR,9bS)-3-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-3a,4,5,6,9a,9b-hexahydrobenzo[g][1]benzofuran-6-yl] (E)-2-methylbut-2-enoate
IUPAC Name:	[(3R,3aR,5aS,6R,9aR,9bS)-3-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-3a,4,5,6,9a,9b-hexahydrobenzo[g][1]benzofuran-6-yl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	OBOBZPIEGNNVAR-GQOPTAQWSA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-6-11(2)17(21)24-14-8-7-12(3)15-16-13(9-10-19(14,15)4)20(5,23)18(22)25-16/h6-8,13-16,23H,3,9-10H2,1-2,4-5H3/b11-6+/t13-,14-,15+,16-,19-,20-/m1/s1
SMILES:	C/C=C(\C)/C(=O)O[C@@H]1C=CC(=C)[C@@H]2[C@@]1(CC[C@@H]3[C@H]2OC(=O)[C@]3(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44445436
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO33550	Ferula varia	Species	Apiaceae	Eukaryota	roots	Kyzylkum, Uzbekistan	2001-APR	PMID[18052129]

☑ 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	7

Activity Type	# Activity
Cell Line	4
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100	ug/ml	PMID[18052129]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100	ug/ml	PMID[18052129]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100	ug/ml	PMID[18052129]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	>	100	ug/ml	PMID[18052129]
NPT2	Others	Unspecified		IC50	>	100	ug/ml	PMID[18052129]

☑ 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 NPC477125 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	194
0.1-0.2	921
0.2-0.3	3310
0.3-0.4	6663
0.4-0.5	13623
0.5-0.6	7739
0.6-0.7	7177
0.7-0.8	2891
0.8-0.85	162
0.85-0.9	11
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.932	High Similarity	NPC179798
0.932	High Similarity	NPC304180
0.9143	High Similarity	NPC469463
0.9143	High Similarity	NPC469496
0.9143	High Similarity	NPC56448
0.9143	High Similarity	NPC469454
0.9038	High Similarity	NPC5103
0.8969	High Similarity	NPC477129
0.8969	High Similarity	NPC477130
0.8889	High Similarity	NPC23046
0.8738	High Similarity	NPC146731
0.8571	High Similarity	NPC303697
0.8558	High Similarity	NPC258532
0.8558	High Similarity	NPC296950
0.85	High Similarity	NPC183012
0.85	High Similarity	NPC295347
0.8491	Intermediate Similarity	NPC475418
0.8491	Intermediate Similarity	NPC473482
0.8491	Intermediate Similarity	NPC318363
0.8454	Intermediate Similarity	NPC477128
0.8411	Intermediate Similarity	NPC475065
0.8396	Intermediate Similarity	NPC329048
0.8396	Intermediate Similarity	NPC67321
0.8396	Intermediate Similarity	NPC187435
0.8396	Intermediate Similarity	NPC330011
0.8384	Intermediate Similarity	NPC186363
0.8384	Intermediate Similarity	NPC233345
0.8384	Intermediate Similarity	NPC252433
0.8365	Intermediate Similarity	NPC469606
0.8365	Intermediate Similarity	NPC273005
0.8365	Intermediate Similarity	NPC31058
0.8349	Intermediate Similarity	NPC269530
0.8333	Intermediate Similarity	NPC208094
0.8333	Intermediate Similarity	NPC235014
0.8304	Intermediate Similarity	NPC284707
0.8302	Intermediate Similarity	NPC173172
0.8302	Intermediate Similarity	NPC469607
0.8302	Intermediate Similarity	NPC1679
0.8302	Intermediate Similarity	NPC475414
0.8288	Intermediate Similarity	NPC270478
0.8286	Intermediate Similarity	NPC23584
0.8283	Intermediate Similarity	NPC212679
0.8283	Intermediate Similarity	NPC469595
0.8283	Intermediate Similarity	NPC220454
0.8273	Intermediate Similarity	NPC471204
0.8273	Intermediate Similarity	NPC477126
0.8269	Intermediate Similarity	NPC469657
0.8269	Intermediate Similarity	NPC244456
0.8265	Intermediate Similarity	NPC215831
0.8252	Intermediate Similarity	NPC159763
0.8252	Intermediate Similarity	NPC316598
0.8252	Intermediate Similarity	NPC216478
0.8252	Intermediate Similarity	NPC278386
0.8252	Intermediate Similarity	NPC124512
0.8241	Intermediate Similarity	NPC228477
0.8241	Intermediate Similarity	NPC137911
0.8224	Intermediate Similarity	NPC131665
0.8224	Intermediate Similarity	NPC255387
0.8224	Intermediate Similarity	NPC475176
0.8224	Intermediate Similarity	NPC469853
0.8218	Intermediate Similarity	NPC38830
0.8214	Intermediate Similarity	NPC53396
0.8214	Intermediate Similarity	NPC98249
0.82	Intermediate Similarity	NPC72845
0.819	Intermediate Similarity	NPC11956
0.819	Intermediate Similarity	NPC155332
0.819	Intermediate Similarity	NPC114540
0.819	Intermediate Similarity	NPC476081
0.819	Intermediate Similarity	NPC32577
0.8182	Intermediate Similarity	NPC73995
0.8182	Intermediate Similarity	NPC168131
0.8173	Intermediate Similarity	NPC474012
0.8173	Intermediate Similarity	NPC47024
0.8173	Intermediate Similarity	NPC476299
0.8165	Intermediate Similarity	NPC210005
0.8155	Intermediate Similarity	NPC91695
0.8155	Intermediate Similarity	NPC70145
0.8155	Intermediate Similarity	NPC73911
0.8148	Intermediate Similarity	NPC306265
0.8148	Intermediate Similarity	NPC264819
0.8142	Intermediate Similarity	NPC50774
0.8142	Intermediate Similarity	NPC311554
0.8142	Intermediate Similarity	NPC709
0.8142	Intermediate Similarity	NPC186525
0.8142	Intermediate Similarity	NPC257457
0.8131	Intermediate Similarity	NPC34768
0.8131	Intermediate Similarity	NPC472645
0.8125	Intermediate Similarity	NPC477509
0.8125	Intermediate Similarity	NPC64318
0.8119	Intermediate Similarity	NPC152778
0.8119	Intermediate Similarity	NPC205034
0.8119	Intermediate Similarity	NPC162615
0.8119	Intermediate Similarity	NPC139692
0.8113	Intermediate Similarity	NPC473624
0.8113	Intermediate Similarity	NPC159533
0.8108	Intermediate Similarity	NPC474271
0.81	Intermediate Similarity	NPC472307
0.81	Intermediate Similarity	NPC469372
0.81	Intermediate Similarity	NPC15059
0.8095	Intermediate Similarity	NPC303559
0.8091	Intermediate Similarity	NPC317107
0.8091	Intermediate Similarity	NPC188738
0.8081	Intermediate Similarity	NPC277771
0.8081	Intermediate Similarity	NPC477302
0.8081	Intermediate Similarity	NPC226863
0.8077	Intermediate Similarity	NPC57079
0.8077	Intermediate Similarity	NPC108368
0.8077	Intermediate Similarity	NPC222303
0.8077	Intermediate Similarity	NPC278008
0.8073	Intermediate Similarity	NPC5475
0.8073	Intermediate Similarity	NPC472216
0.8073	Intermediate Similarity	NPC42662
0.8073	Intermediate Similarity	NPC284828
0.8073	Intermediate Similarity	NPC173905
0.8073	Intermediate Similarity	NPC469370
0.807	Intermediate Similarity	NPC305260
0.807	Intermediate Similarity	NPC476529
0.807	Intermediate Similarity	NPC475775
0.807	Intermediate Similarity	NPC270850
0.8061	Intermediate Similarity	NPC9231
0.8058	Intermediate Similarity	NPC473153
0.8056	Intermediate Similarity	NPC473284
0.8056	Intermediate Similarity	NPC302788
0.8056	Intermediate Similarity	NPC144854
0.8056	Intermediate Similarity	NPC475294
0.8056	Intermediate Similarity	NPC3316
0.8056	Intermediate Similarity	NPC301666
0.8053	Intermediate Similarity	NPC473590
0.8053	Intermediate Similarity	NPC183580
0.8053	Intermediate Similarity	NPC469684
0.8053	Intermediate Similarity	NPC286528
0.8053	Intermediate Similarity	NPC20302
0.8053	Intermediate Similarity	NPC167606
0.8053	Intermediate Similarity	NPC140055
0.8053	Intermediate Similarity	NPC470492
0.8053	Intermediate Similarity	NPC470493
0.8053	Intermediate Similarity	NPC312824
0.8039	Intermediate Similarity	NPC470697
0.8037	Intermediate Similarity	NPC473175
0.8037	Intermediate Similarity	NPC118911
0.8037	Intermediate Similarity	NPC477127
0.8036	Intermediate Similarity	NPC67259
0.8036	Intermediate Similarity	NPC147912
0.8034	Intermediate Similarity	NPC24651
0.8019	Intermediate Similarity	NPC472552
0.8019	Intermediate Similarity	NPC295791
0.8018	Intermediate Similarity	NPC476801
0.8018	Intermediate Similarity	NPC317687
0.8018	Intermediate Similarity	NPC475524
0.8018	Intermediate Similarity	NPC100267
0.8018	Intermediate Similarity	NPC236217
0.8	Intermediate Similarity	NPC173042
0.8	Intermediate Similarity	NPC286880
0.8	Intermediate Similarity	NPC107338
0.8	Intermediate Similarity	NPC284561
0.8	Intermediate Similarity	NPC82876
0.8	Intermediate Similarity	NPC474585
0.8	Intermediate Similarity	NPC473627
0.8	Intermediate Similarity	NPC29133
0.8	Intermediate Similarity	NPC475885
0.8	Intermediate Similarity	NPC474370
0.8	Intermediate Similarity	NPC206001
0.8	Intermediate Similarity	NPC118011
0.8	Intermediate Similarity	NPC478211
0.8	Intermediate Similarity	NPC119550
0.8	Intermediate Similarity	NPC174314
0.8	Intermediate Similarity	NPC253906
0.8	Intermediate Similarity	NPC37116
0.8	Intermediate Similarity	NPC5509
0.8	Intermediate Similarity	NPC475134
0.8	Intermediate Similarity	NPC218927
0.8	Intermediate Similarity	NPC475563
0.8	Intermediate Similarity	NPC36668
0.8	Intermediate Similarity	NPC109607
0.7982	Intermediate Similarity	NPC275539
0.7982	Intermediate Similarity	NPC189075
0.7982	Intermediate Similarity	NPC154608
0.7982	Intermediate Similarity	NPC153440
0.7982	Intermediate Similarity	NPC192813
0.7982	Intermediate Similarity	NPC277017
0.7981	Intermediate Similarity	NPC110937
0.7981	Intermediate Similarity	NPC38530
0.7981	Intermediate Similarity	NPC202705
0.7981	Intermediate Similarity	NPC474343
0.7981	Intermediate Similarity	NPC84335
0.7966	Intermediate Similarity	NPC181999
0.7965	Intermediate Similarity	NPC478216
0.7965	Intermediate Similarity	NPC190286
0.7965	Intermediate Similarity	NPC176840
0.7965	Intermediate Similarity	NPC179626
0.7963	Intermediate Similarity	NPC266570
0.7963	Intermediate Similarity	NPC252296
0.7961	Intermediate Similarity	NPC209355
0.7961	Intermediate Similarity	NPC316215
0.7959	Intermediate Similarity	NPC177932
0.7949	Intermediate Similarity	NPC67251
0.7946	Intermediate Similarity	NPC25909
0.7946	Intermediate Similarity	NPC49451
0.7944	Intermediate Similarity	NPC4620
0.7944	Intermediate Similarity	NPC471364

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 NPC477125 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1141
0.2-0.3	3256
0.3-0.4	2786
0.4-0.5	1143
0.5-0.6	370
0.6-0.7	199
0.7-0.8	90
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8252	Intermediate Similarity	NPD4225	Approved
0.8053	Intermediate Similarity	NPD7115	Discovery
0.7959	Intermediate Similarity	NPD1694	Approved
0.7727	Intermediate Similarity	NPD5697	Approved
0.7699	Intermediate Similarity	NPD8297	Approved
0.7658	Intermediate Similarity	NPD6881	Approved
0.7658	Intermediate Similarity	NPD6899	Approved
0.7611	Intermediate Similarity	NPD6649	Approved
0.7611	Intermediate Similarity	NPD6650	Approved
0.7589	Intermediate Similarity	NPD6012	Approved
0.7589	Intermediate Similarity	NPD6014	Approved
0.7589	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6013	Approved
0.7522	Intermediate Similarity	NPD7102	Approved
0.7522	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD7290	Approved
0.7522	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.7478	Intermediate Similarity	NPD4632	Approved
0.7477	Intermediate Similarity	NPD5739	Approved
0.7477	Intermediate Similarity	NPD6675	Approved
0.7477	Intermediate Similarity	NPD7128	Approved
0.7477	Intermediate Similarity	NPD6402	Approved
0.7475	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD8130	Phase 1
0.7456	Intermediate Similarity	NPD6617	Approved
0.7456	Intermediate Similarity	NPD6869	Approved
0.7456	Intermediate Similarity	NPD6847	Approved
0.7453	Intermediate Similarity	NPD5695	Phase 3
0.7434	Intermediate Similarity	NPD6373	Approved
0.7434	Intermediate Similarity	NPD6372	Approved
0.7411	Intermediate Similarity	NPD5701	Approved
0.7411	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5696	Approved
0.7395	Intermediate Similarity	NPD6319	Approved
0.7391	Intermediate Similarity	NPD6882	Approved
0.7364	Intermediate Similarity	NPD5211	Phase 2
0.7345	Intermediate Similarity	NPD7320	Approved
0.7339	Intermediate Similarity	NPD5285	Approved
0.7339	Intermediate Similarity	NPD5286	Approved
0.7339	Intermediate Similarity	NPD4696	Approved
0.7333	Intermediate Similarity	NPD5281	Approved
0.7333	Intermediate Similarity	NPD5284	Approved
0.7315	Intermediate Similarity	NPD6083	Phase 2
0.7315	Intermediate Similarity	NPD6084	Phase 2
0.7315	Intermediate Similarity	NPD7902	Approved
0.729	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6399	Phase 3
0.7257	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7638	Approved
0.7232	Intermediate Similarity	NPD5141	Approved
0.7222	Intermediate Similarity	NPD7260	Phase 2
0.7207	Intermediate Similarity	NPD5224	Approved
0.7207	Intermediate Similarity	NPD5225	Approved
0.7207	Intermediate Similarity	NPD4633	Approved
0.7207	Intermediate Similarity	NPD5226	Approved
0.7196	Intermediate Similarity	NPD7748	Approved
0.7193	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7503	Approved
0.7182	Intermediate Similarity	NPD7640	Approved
0.7182	Intermediate Similarity	NPD6648	Approved
0.7182	Intermediate Similarity	NPD7639	Approved
0.717	Intermediate Similarity	NPD6411	Approved
0.717	Intermediate Similarity	NPD5694	Approved
0.717	Intermediate Similarity	NPD5693	Phase 1
0.7156	Intermediate Similarity	NPD4755	Approved
0.7154	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD5174	Approved
0.713	Intermediate Similarity	NPD5210	Approved
0.713	Intermediate Similarity	NPD4629	Approved
0.7117	Intermediate Similarity	NPD5344	Discontinued
0.7117	Intermediate Similarity	NPD5223	Approved
0.7107	Intermediate Similarity	NPD6054	Approved
0.7103	Intermediate Similarity	NPD5779	Approved
0.7103	Intermediate Similarity	NPD5778	Approved
0.7097	Intermediate Similarity	NPD6616	Approved
0.7075	Intermediate Similarity	NPD5207	Approved
0.7075	Intermediate Similarity	NPD7838	Discovery
0.7075	Intermediate Similarity	NPD5692	Phase 3
0.7075	Intermediate Similarity	NPD46	Approved
0.7075	Intermediate Similarity	NPD6698	Approved
0.7069	Intermediate Similarity	NPD6371	Approved
0.7069	Intermediate Similarity	NPD4634	Approved
0.7064	Intermediate Similarity	NPD5222	Approved
0.7064	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5221	Approved
0.7059	Intermediate Similarity	NPD6274	Approved
0.7049	Intermediate Similarity	NPD5983	Phase 2
0.7049	Intermediate Similarity	NPD8513	Phase 3
0.7049	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8515	Approved
0.7049	Intermediate Similarity	NPD6015	Approved
0.7049	Intermediate Similarity	NPD8516	Approved
0.7049	Intermediate Similarity	NPD6016	Approved
0.7049	Intermediate Similarity	NPD8517	Approved
0.7048	Intermediate Similarity	NPD6672	Approved
0.7048	Intermediate Similarity	NPD5737	Approved
0.704	Intermediate Similarity	NPD7078	Approved
0.7037	Intermediate Similarity	NPD7900	Approved
0.7037	Intermediate Similarity	NPD5282	Discontinued
0.7037	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4700	Approved
0.7025	Intermediate Similarity	NPD7100	Approved
0.7025	Intermediate Similarity	NPD7101	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.7019	Intermediate Similarity	NPD5279	Phase 3
0.7018	Intermediate Similarity	NPD6008	Approved
0.7009	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7009	Intermediate Similarity	NPD6050	Approved
0.7	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD6317	Approved
0.6992	Remote Similarity	NPD5988	Approved
0.6992	Remote Similarity	NPD6370	Approved
0.6984	Remote Similarity	NPD7736	Approved
0.6981	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6101	Approved
0.6981	Remote Similarity	NPD4753	Phase 2
0.6972	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7507	Approved
0.6952	Remote Similarity	NPD3573	Approved
0.6942	Remote Similarity	NPD6335	Approved
0.6942	Remote Similarity	NPD6313	Approved
0.6942	Remote Similarity	NPD6314	Approved
0.6937	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7604	Phase 2
0.6931	Remote Similarity	NPD4695	Discontinued
0.6916	Remote Similarity	NPD5785	Approved
0.6909	Remote Similarity	NPD4697	Phase 3
0.6899	Remote Similarity	NPD6845	Suspended
0.6897	Remote Similarity	NPD4730	Approved
0.6897	Remote Similarity	NPD4729	Approved
0.6857	Remote Similarity	NPD7334	Approved
0.6857	Remote Similarity	NPD6409	Approved
0.6857	Remote Similarity	NPD5330	Approved
0.6857	Remote Similarity	NPD6684	Approved
0.6857	Remote Similarity	NPD7146	Approved
0.6857	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7521	Approved
0.6857	Remote Similarity	NPD5280	Approved
0.6857	Remote Similarity	NPD4694	Approved
0.6857	Remote Similarity	NPD5690	Phase 2
0.6852	Remote Similarity	NPD6079	Approved
0.6829	Remote Similarity	NPD6059	Approved
0.6825	Remote Similarity	NPD6336	Discontinued
0.6822	Remote Similarity	NPD6673	Approved
0.6822	Remote Similarity	NPD6904	Approved
0.6822	Remote Similarity	NPD6080	Approved
0.681	Remote Similarity	NPD6412	Phase 2
0.6807	Remote Similarity	NPD6053	Discontinued
0.68	Remote Similarity	NPD8328	Phase 3
0.6797	Remote Similarity	NPD7319	Approved
0.6789	Remote Similarity	NPD4202	Approved
0.678	Remote Similarity	NPD5248	Approved
0.678	Remote Similarity	NPD5247	Approved
0.678	Remote Similarity	NPD5251	Approved
0.678	Remote Similarity	NPD5249	Phase 3
0.678	Remote Similarity	NPD5250	Approved
0.6777	Remote Similarity	NPD6868	Approved
0.6772	Remote Similarity	NPD8293	Discontinued
0.6772	Remote Similarity	NPD8074	Phase 3
0.6768	Remote Similarity	NPD8039	Approved
0.6762	Remote Similarity	NPD1696	Phase 3
0.6752	Remote Similarity	NPD5128	Approved
0.6729	Remote Similarity	NPD6903	Approved
0.6729	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6001	Approved
0.6724	Remote Similarity	NPD4767	Approved
0.6724	Remote Similarity	NPD4768	Approved
0.6723	Remote Similarity	NPD5215	Approved
0.6723	Remote Similarity	NPD5217	Approved
0.6723	Remote Similarity	NPD5216	Approved
0.6698	Remote Similarity	NPD4519	Discontinued
0.6698	Remote Similarity	NPD4623	Approved
0.6697	Remote Similarity	NPD8035	Phase 2
0.6697	Remote Similarity	NPD7637	Suspended
0.6697	Remote Similarity	NPD8034	Phase 2
0.6697	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD5654	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.664	Remote Similarity	NPD8033	Approved
0.664	Remote Similarity	NPD6909	Approved
0.664	Remote Similarity	NPD6908	Approved
0.6639	Remote Similarity	NPD5135	Approved
0.6639	Remote Similarity	NPD5169	Approved
0.6639	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3667	Approved
0.6635	Remote Similarity	NPD5209	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