NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	454.26
Volume:	466.323
LogP:	1.331
LogD:	0.303
LogS:	-2.119
# Rotatable Bonds:	9
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.393
Synthetic Accessibility Score:	5.064
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.22
MDCK Permeability:	4.057185651618056e-05
Pgp-inhibitor:	0.114
Pgp-substrate:	0.943
Human Intestinal Absorption (HIA):	0.136
20% Bioavailability (F20%):	0.902
30% Bioavailability (F30%):	0.082

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.637
Plasma Protein Binding (PPB):	31.55564308166504%
Volume Distribution (VD):	0.573
Pgp-substrate:	56.839752197265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.292
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.408
CYP3A4-substrate:	0.468

ADMET: Excretion

Clearance (CL):	2.114
Half-life (T1/2):	0.632

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.723
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.915
Maximum Recommended Daily Dose:	0.181
Skin Sensitization:	0.05
Carcinogencity:	0.267
Eye Corrosion:	0.038
Eye Irritation:	0.036
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC477437

Natural Product ID:	NPC477437
*Common Name:**	[(1S,2R,4aS,8S,8aR)-8-acetyloxy-5-(3,5-dihydroxy-3-methylpentyl)-2-hydroxy-1,4a,6-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]methyl acetate
IUPAC Name:	[(1S,2R,4aS,8S,8aR)-8-acetyloxy-5-(3,5-dihydroxy-3-methylpentyl)-2-hydroxy-1,4a,6-trimethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]methyl acetate
Synonyms:
Standard InCHIKey:	SGWHOCKDQUUVNF-SDTSKVPRSA-N
Standard InCHI:	InChI=1S/C24H38O8/c1-14-17(7-9-22(4,30)11-12-25)23(5)10-8-18(28)24(6,13-31-15(2)26)21(23)20(19(14)29)32-16(3)27/h18,20-21,25,28,30H,7-13H2,1-6H3/t18-,20-,21-,22?,23-,24+/m1/s1
SMILES:	CC1=C([C@]2(CC[C@H]([C@]([C@@H]2[C@@H](C1=O)OC(=O)C)(C)COC(=O)C)O)C)CCC(C)(CCO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122187011
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO33600	Leonurus macranthus	Species	Lamiaceae	Eukaryota	aerial parts	Huanren, Liaoning Province, China	2013-AUG	PMID[26348503]

☑ 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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	<	50	%	PMID[26348503]

☑ 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 NPC477437 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	230
0.1-0.2	1503
0.2-0.3	5229
0.3-0.4	9642
0.4-0.5	12008
0.5-0.6	7021
0.6-0.7	5504
0.7-0.8	1507
0.8-0.85	45
0.85-0.9	3
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477438
0.9886	High Similarity	NPC477439
0.9773	High Similarity	NPC477435
0.9773	High Similarity	NPC477436
0.875	High Similarity	NPC472972
0.8673	High Similarity	NPC70967
0.8673	High Similarity	NPC33973
0.8617	High Similarity	NPC212812
0.8602	High Similarity	NPC248913
0.8586	High Similarity	NPC135854
0.8586	High Similarity	NPC470251
0.8586	High Similarity	NPC2436
0.8586	High Similarity	NPC216245
0.8469	Intermediate Similarity	NPC124211
0.8438	Intermediate Similarity	NPC96859
0.8438	Intermediate Similarity	NPC305483
0.8438	Intermediate Similarity	NPC328162
0.8416	Intermediate Similarity	NPC44063
0.84	Intermediate Similarity	NPC65523
0.8384	Intermediate Similarity	NPC119601
0.8384	Intermediate Similarity	NPC53222
0.8384	Intermediate Similarity	NPC308726
0.8381	Intermediate Similarity	NPC473798
0.8367	Intermediate Similarity	NPC157787
0.8367	Intermediate Similarity	NPC88198
0.8365	Intermediate Similarity	NPC90769
0.8351	Intermediate Similarity	NPC285513
0.8333	Intermediate Similarity	NPC317586
0.8333	Intermediate Similarity	NPC476479
0.8333	Intermediate Similarity	NPC134067
0.8333	Intermediate Similarity	NPC293850
0.8333	Intermediate Similarity	NPC470016
0.8302	Intermediate Similarity	NPC134869
0.8302	Intermediate Similarity	NPC40632
0.8302	Intermediate Similarity	NPC96312
0.8302	Intermediate Similarity	NPC328374
0.8302	Intermediate Similarity	NPC152199
0.8302	Intermediate Similarity	NPC235539
0.8302	Intermediate Similarity	NPC251236
0.83	Intermediate Similarity	NPC179208
0.8283	Intermediate Similarity	NPC302537
0.8283	Intermediate Similarity	NPC469327
0.8283	Intermediate Similarity	NPC163372
0.828	Intermediate Similarity	NPC185059
0.828	Intermediate Similarity	NPC475001
0.8252	Intermediate Similarity	NPC2766
0.8252	Intermediate Similarity	NPC286174
0.8252	Intermediate Similarity	NPC77947
0.8229	Intermediate Similarity	NPC166906
0.8229	Intermediate Similarity	NPC169751
0.8229	Intermediate Similarity	NPC272635
0.8229	Intermediate Similarity	NPC240617
0.8218	Intermediate Similarity	NPC118911
0.8211	Intermediate Similarity	NPC235704
0.8211	Intermediate Similarity	NPC99380
0.8208	Intermediate Similarity	NPC18547
0.8208	Intermediate Similarity	NPC474906
0.82	Intermediate Similarity	NPC80781
0.819	Intermediate Similarity	NPC474516
0.8173	Intermediate Similarity	NPC129689
0.8173	Intermediate Similarity	NPC473036
0.8173	Intermediate Similarity	NPC272898
0.8163	Intermediate Similarity	NPC254496
0.8163	Intermediate Similarity	NPC216904
0.8163	Intermediate Similarity	NPC43747
0.8155	Intermediate Similarity	NPC94942
0.8148	Intermediate Similarity	NPC297179
0.8144	Intermediate Similarity	NPC139570
0.8137	Intermediate Similarity	NPC472645
0.8137	Intermediate Similarity	NPC181357
0.8132	Intermediate Similarity	NPC64600
0.8131	Intermediate Similarity	NPC16081
0.8131	Intermediate Similarity	NPC173686
0.8125	Intermediate Similarity	NPC109414
0.8119	Intermediate Similarity	NPC275583
0.8113	Intermediate Similarity	NPC49451
0.8113	Intermediate Similarity	NPC198539
0.8113	Intermediate Similarity	NPC7921
0.8113	Intermediate Similarity	NPC208998
0.81	Intermediate Similarity	NPC472643
0.8095	Intermediate Similarity	NPC43775
0.8095	Intermediate Similarity	NPC115303
0.8095	Intermediate Similarity	NPC146945
0.8095	Intermediate Similarity	NPC171888
0.8095	Intermediate Similarity	NPC34315
0.8085	Intermediate Similarity	NPC230387
0.8081	Intermediate Similarity	NPC112753
0.8081	Intermediate Similarity	NPC275439
0.8077	Intermediate Similarity	NPC41405
0.8065	Intermediate Similarity	NPC73038
0.8065	Intermediate Similarity	NPC475181
0.8065	Intermediate Similarity	NPC229717
0.8061	Intermediate Similarity	NPC95565
0.8061	Intermediate Similarity	NPC157113
0.8061	Intermediate Similarity	NPC62516
0.8058	Intermediate Similarity	NPC144854
0.8058	Intermediate Similarity	NPC3316
0.8041	Intermediate Similarity	NPC293086
0.8041	Intermediate Similarity	NPC184870
0.8039	Intermediate Similarity	NPC213366
0.8037	Intermediate Similarity	NPC323821
0.8037	Intermediate Similarity	NPC45218
0.8037	Intermediate Similarity	NPC143268
0.8037	Intermediate Similarity	NPC268238
0.802	Intermediate Similarity	NPC295791
0.802	Intermediate Similarity	NPC136289
0.8019	Intermediate Similarity	NPC289312
0.8019	Intermediate Similarity	NPC11252
0.8	Intermediate Similarity	NPC316964
0.8	Intermediate Similarity	NPC476274
0.8	Intermediate Similarity	NPC472644
0.8	Intermediate Similarity	NPC293890
0.8	Intermediate Similarity	NPC198880
0.7982	Intermediate Similarity	NPC17772
0.7981	Intermediate Similarity	NPC469916
0.7981	Intermediate Similarity	NPC322903
0.7981	Intermediate Similarity	NPC154608
0.7981	Intermediate Similarity	NPC472439
0.7981	Intermediate Similarity	NPC192813
0.7981	Intermediate Similarity	NPC277017
0.798	Intermediate Similarity	NPC18509
0.798	Intermediate Similarity	NPC175351
0.798	Intermediate Similarity	NPC224356
0.798	Intermediate Similarity	NPC18319
0.798	Intermediate Similarity	NPC473456
0.798	Intermediate Similarity	NPC121402
0.798	Intermediate Similarity	NPC132753
0.798	Intermediate Similarity	NPC151681
0.7963	Intermediate Similarity	NPC270958
0.7961	Intermediate Similarity	NPC111952
0.7961	Intermediate Similarity	NPC51452
0.7961	Intermediate Similarity	NPC475494
0.7961	Intermediate Similarity	NPC1679
0.7959	Intermediate Similarity	NPC255809
0.7959	Intermediate Similarity	NPC469329
0.7959	Intermediate Similarity	NPC37787
0.7959	Intermediate Similarity	NPC473170
0.7959	Intermediate Similarity	NPC473415
0.7959	Intermediate Similarity	NPC180557
0.7959	Intermediate Similarity	NPC30677
0.7957	Intermediate Similarity	NPC197823
0.7944	Intermediate Similarity	NPC472926
0.7944	Intermediate Similarity	NPC159333
0.7944	Intermediate Similarity	NPC25909
0.7944	Intermediate Similarity	NPC194100
0.7944	Intermediate Similarity	NPC202889
0.7941	Intermediate Similarity	NPC264048
0.7941	Intermediate Similarity	NPC251017
0.7941	Intermediate Similarity	NPC90177
0.7938	Intermediate Similarity	NPC295643
0.7938	Intermediate Similarity	NPC214756
0.7938	Intermediate Similarity	NPC271652
0.7938	Intermediate Similarity	NPC272075
0.7938	Intermediate Similarity	NPC79117
0.7925	Intermediate Similarity	NPC201992
0.7921	Intermediate Similarity	NPC224720
0.7921	Intermediate Similarity	NPC476240
0.7921	Intermediate Similarity	NPC476223
0.7921	Intermediate Similarity	NPC115862
0.7921	Intermediate Similarity	NPC118964
0.7921	Intermediate Similarity	NPC81530
0.7917	Intermediate Similarity	NPC134321
0.7917	Intermediate Similarity	NPC128672
0.7917	Intermediate Similarity	NPC20388
0.7912	Intermediate Similarity	NPC473420
0.7909	Intermediate Similarity	NPC470777
0.7909	Intermediate Similarity	NPC472933
0.7905	Intermediate Similarity	NPC27814
0.79	Intermediate Similarity	NPC478056
0.79	Intermediate Similarity	NPC260149
0.79	Intermediate Similarity	NPC58942
0.7895	Intermediate Similarity	NPC473229
0.789	Intermediate Similarity	NPC97908
0.789	Intermediate Similarity	NPC122033
0.789	Intermediate Similarity	NPC471854
0.789	Intermediate Similarity	NPC309433
0.789	Intermediate Similarity	NPC470854
0.789	Intermediate Similarity	NPC474654
0.789	Intermediate Similarity	NPC287343
0.7885	Intermediate Similarity	NPC475294
0.7885	Intermediate Similarity	NPC202524
0.7885	Intermediate Similarity	NPC471783
0.7885	Intermediate Similarity	NPC112780
0.7885	Intermediate Similarity	NPC9457
0.7885	Intermediate Similarity	NPC143609
0.7879	Intermediate Similarity	NPC476318
0.7879	Intermediate Similarity	NPC219353
0.7879	Intermediate Similarity	NPC471822
0.7879	Intermediate Similarity	NPC327179
0.7879	Intermediate Similarity	NPC476327
0.7879	Intermediate Similarity	NPC154526
0.7879	Intermediate Similarity	NPC7124
0.7879	Intermediate Similarity	NPC472362
0.7879	Intermediate Similarity	NPC471777
0.7879	Intermediate Similarity	NPC472363
0.7879	Intermediate Similarity	NPC98874
0.7879	Intermediate Similarity	NPC328371
0.7872	Intermediate Similarity	NPC56588
0.7872	Intermediate Similarity	NPC473226
0.7872	Intermediate Similarity	NPC202394

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 NPC477437 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	2048
0.2-0.3	3696
0.3-0.4	2046
0.4-0.5	685
0.5-0.6	242
0.6-0.7	135
0.7-0.8	75
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8687	High Similarity	NPD6402	Approved
0.8687	High Similarity	NPD6675	Approved
0.8687	High Similarity	NPD5739	Approved
0.8687	High Similarity	NPD7128	Approved
0.8614	High Similarity	NPD6372	Approved
0.8614	High Similarity	NPD6373	Approved
0.8515	High Similarity	NPD6881	Approved
0.8515	High Similarity	NPD6899	Approved
0.8515	High Similarity	NPD7320	Approved
0.8447	Intermediate Similarity	NPD6649	Approved
0.8447	Intermediate Similarity	NPD6650	Approved
0.8416	Intermediate Similarity	NPD5697	Approved
0.8416	Intermediate Similarity	NPD5701	Approved
0.8365	Intermediate Similarity	NPD8297	Approved
0.8365	Intermediate Similarity	NPD6882	Approved
0.835	Intermediate Similarity	NPD7102	Approved
0.835	Intermediate Similarity	NPD7290	Approved
0.835	Intermediate Similarity	NPD6883	Approved
0.8269	Intermediate Similarity	NPD6847	Approved
0.8269	Intermediate Similarity	NPD8130	Phase 1
0.8269	Intermediate Similarity	NPD6869	Approved
0.8269	Intermediate Similarity	NPD6617	Approved
0.8252	Intermediate Similarity	NPD6014	Approved
0.8252	Intermediate Similarity	NPD6012	Approved
0.8252	Intermediate Similarity	NPD6013	Approved
0.8155	Intermediate Similarity	NPD6011	Approved
0.8095	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD6084	Phase 2
0.798	Intermediate Similarity	NPD4755	Approved
0.798	Intermediate Similarity	NPD6083	Phase 2
0.7857	Intermediate Similarity	NPD7748	Approved
0.7835	Intermediate Similarity	NPD7515	Phase 2
0.7822	Intermediate Similarity	NPD5286	Approved
0.7822	Intermediate Similarity	NPD4700	Approved
0.7822	Intermediate Similarity	NPD4696	Approved
0.7822	Intermediate Similarity	NPD5285	Approved
0.78	Intermediate Similarity	NPD7902	Approved
0.7798	Intermediate Similarity	NPD6274	Approved
0.7778	Intermediate Similarity	NPD5695	Phase 3
0.7748	Intermediate Similarity	NPD7100	Approved
0.7748	Intermediate Similarity	NPD7101	Approved
0.7679	Intermediate Similarity	NPD6319	Approved
0.767	Intermediate Similarity	NPD5225	Approved
0.767	Intermediate Similarity	NPD5211	Phase 2
0.767	Intermediate Similarity	NPD4633	Approved
0.767	Intermediate Similarity	NPD5224	Approved
0.767	Intermediate Similarity	NPD5226	Approved
0.7658	Intermediate Similarity	NPD6335	Approved
0.7629	Intermediate Similarity	NPD5328	Approved
0.7619	Intermediate Similarity	NPD4768	Approved
0.7619	Intermediate Similarity	NPD4767	Approved
0.7611	Intermediate Similarity	NPD6909	Approved
0.7611	Intermediate Similarity	NPD6908	Approved
0.7596	Intermediate Similarity	NPD5174	Approved
0.7596	Intermediate Similarity	NPD5175	Approved
0.7576	Intermediate Similarity	NPD6399	Phase 3
0.7573	Intermediate Similarity	NPD5223	Approved
0.7568	Intermediate Similarity	NPD6317	Approved
0.7568	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD5696	Approved
0.7526	Intermediate Similarity	NPD6672	Approved
0.7526	Intermediate Similarity	NPD5737	Approved
0.7525	Intermediate Similarity	NPD4697	Phase 3
0.7525	Intermediate Similarity	NPD5221	Approved
0.7525	Intermediate Similarity	NPD5222	Approved
0.7525	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5141	Approved
0.75	Intermediate Similarity	NPD6313	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6314	Approved
0.7478	Intermediate Similarity	NPD8328	Phase 3
0.7477	Intermediate Similarity	NPD4729	Approved
0.7477	Intermediate Similarity	NPD6868	Approved
0.7477	Intermediate Similarity	NPD4730	Approved
0.7475	Intermediate Similarity	NPD6079	Approved
0.7475	Intermediate Similarity	NPD6411	Approved
0.7455	Intermediate Similarity	NPD4632	Approved
0.7451	Intermediate Similarity	NPD5173	Approved
0.7429	Intermediate Similarity	NPD4754	Approved
0.7423	Intermediate Similarity	NPD3573	Approved
0.7414	Intermediate Similarity	NPD7492	Approved
0.7411	Intermediate Similarity	NPD6009	Approved
0.7368	Intermediate Similarity	NPD6054	Approved
0.7368	Intermediate Similarity	NPD6059	Approved
0.735	Intermediate Similarity	NPD6616	Approved
0.7339	Intermediate Similarity	NPD5251	Approved
0.7339	Intermediate Similarity	NPD5249	Phase 3
0.7339	Intermediate Similarity	NPD5250	Approved
0.7339	Intermediate Similarity	NPD5247	Approved
0.7339	Intermediate Similarity	NPD5248	Approved
0.7328	Intermediate Similarity	NPD7604	Phase 2
0.732	Intermediate Similarity	NPD3618	Phase 1
0.7315	Intermediate Similarity	NPD5128	Approved
0.7304	Intermediate Similarity	NPD5983	Phase 2
0.729	Intermediate Similarity	NPD6008	Approved
0.7288	Intermediate Similarity	NPD7078	Approved
0.7288	Intermediate Similarity	NPD8293	Discontinued
0.7273	Intermediate Similarity	NPD6080	Approved
0.7273	Intermediate Similarity	NPD6673	Approved
0.7273	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4753	Phase 2
0.7273	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6101	Approved
0.7273	Intermediate Similarity	NPD6904	Approved
0.7248	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6370	Approved
0.7228	Intermediate Similarity	NPD4202	Approved
0.7227	Intermediate Similarity	NPD7736	Approved
0.7203	Intermediate Similarity	NPD6336	Discontinued
0.7182	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4634	Approved
0.7156	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6015	Approved
0.7155	Intermediate Similarity	NPD6016	Approved
0.7155	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7129	Intermediate Similarity	NPD6050	Approved
0.7117	Intermediate Similarity	NPD5217	Approved
0.7117	Intermediate Similarity	NPD5216	Approved
0.7117	Intermediate Similarity	NPD5215	Approved
0.7113	Intermediate Similarity	NPD4786	Approved
0.7105	Intermediate Similarity	NPD7115	Discovery
0.7094	Intermediate Similarity	NPD5988	Approved
0.7083	Intermediate Similarity	NPD3667	Approved
0.7059	Intermediate Similarity	NPD5779	Approved
0.7059	Intermediate Similarity	NPD5778	Approved
0.7053	Intermediate Similarity	NPD4695	Discontinued
0.7048	Intermediate Similarity	NPD7638	Approved
0.703	Intermediate Similarity	NPD5692	Phase 3
0.7027	Intermediate Similarity	NPD5135	Approved
0.7027	Intermediate Similarity	NPD5169	Approved
0.7027	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3617	Approved
0.7	Intermediate Similarity	NPD6903	Approved
0.7	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7640	Approved
0.6981	Remote Similarity	NPD7639	Approved
0.697	Remote Similarity	NPD6098	Approved
0.697	Remote Similarity	NPD5279	Phase 3
0.6964	Remote Similarity	NPD5127	Approved
0.6961	Remote Similarity	NPD8034	Phase 2
0.6961	Remote Similarity	NPD5693	Phase 1
0.6961	Remote Similarity	NPD5694	Approved
0.6961	Remote Similarity	NPD8035	Phase 2
0.6939	Remote Similarity	NPD3133	Approved
0.6939	Remote Similarity	NPD3666	Approved
0.6939	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD5210	Approved
0.6923	Remote Similarity	NPD4629	Approved
0.6923	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4225	Approved
0.6875	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD1694	Approved
0.6869	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5329	Approved
0.6852	Remote Similarity	NPD7632	Discontinued
0.6847	Remote Similarity	NPD5168	Approved
0.6818	Remote Similarity	NPD7341	Phase 2
0.6803	Remote Similarity	NPD6033	Approved
0.68	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5284	Approved
0.6796	Remote Similarity	NPD5281	Approved
0.6783	Remote Similarity	NPD5167	Approved
0.6777	Remote Similarity	NPD7507	Approved
0.6768	Remote Similarity	NPD4197	Approved
0.6762	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5654	Approved
0.6757	Remote Similarity	NPD6412	Phase 2
0.6754	Remote Similarity	NPD6053	Discontinued
0.6737	Remote Similarity	NPD6116	Phase 1
0.6735	Remote Similarity	NPD6435	Approved
0.67	Remote Similarity	NPD1696	Phase 3
0.6696	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6636	Remote Similarity	NPD5959	Approved
0.6634	Remote Similarity	NPD5280	Approved
0.6634	Remote Similarity	NPD5690	Phase 2
0.6634	Remote Similarity	NPD4694	Approved
0.6632	Remote Similarity	NPD6117	Approved
0.6613	Remote Similarity	NPD7319	Approved
0.66	Remote Similarity	NPD3668	Phase 3
0.6598	Remote Similarity	NPD7645	Phase 2
0.6583	Remote Similarity	NPD6921	Approved
0.6566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4223	Phase 3
0.6566	Remote Similarity	NPD4221	Approved
0.6556	Remote Similarity	NPD3704	Approved
0.6542	Remote Similarity	NPD7614	Phase 1
0.6538	Remote Similarity	NPD46	Approved
0.6538	Remote Similarity	NPD6698	Approved
0.6531	Remote Similarity	NPD5368	Approved
0.6531	Remote Similarity	NPD7525	Registered

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