NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	341.348
LogP:	3.526
LogD:	2.365
LogS:	-3.292
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	5.955
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.176
MDCK Permeability:	1.6502357539138757e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.248
Plasma Protein Binding (PPB):	93.18498992919922%
Volume Distribution (VD):	0.499
Pgp-substrate:	8.258344650268555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.581
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.665
CYP2C9-inhibitor:	0.077
CYP2C9-substrate:	0.175
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	1.101
Half-life (T1/2):	0.301

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.581
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.517
Maximum Recommended Daily Dose:	0.172
Skin Sensitization:	0.772
Carcinogencity:	0.325
Eye Corrosion:	0.784
Eye Irritation:	0.604
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC477852

Natural Product ID:	NPC477852
*Common Name:**	ent-16alpha-Hydroxykaur-11-en-18-oic acid
IUPAC Name:	(1R,4R,5R,9S,10S,13S,14S)-14-hydroxy-5,9,14-trimethyltetracyclo[11.2.1.01,10.04,9]hexadec-11-ene-5-carboxylic acid
Synonyms:
Standard InCHIKey:	PBADTGZBFPSKOQ-XYKGIZQRSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-17-8-4-9-18(2,16(21)22)14(17)7-10-20-11-13(5-6-15(17)20)19(3,23)12-20/h5-6,13-15,23H,4,7-12H2,1-3H3,(H,21,22)/t13-,14-,15-,17+,18-,19+,20-/m1/s1
SMILES:	C[C@]12CCC[C@@]([C@@H]1CC[C@@]34[C@@H]2C=C[C@H](C3)[C@@](C4)(C)O)(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46907075
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO33608	Rhizopus arrhizus	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20481544]

☑ 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	3

Activity Type	# Activity
Cell Line	2
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2796	Individual Protein	Apoptosis regulator Bcl-X	Homo sapiens	IC50	=	380000	nM	PMID[20481544]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	10000	nM	PMID[20481544]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	10000	nM	PMID[20481544]

☑ 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 NPC477852 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	157
0.1-0.2	1081
0.2-0.3	6020
0.3-0.4	16147
0.4-0.5	6606
0.5-0.6	6659
0.6-0.7	4389
0.7-0.8	1483
0.8-0.85	117
0.85-0.9	36
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC147066
0.8889	High Similarity	NPC193347
0.8889	High Similarity	NPC260956
0.8846	High Similarity	NPC69143
0.8795	High Similarity	NPC29447
0.8795	High Similarity	NPC269638
0.8765	High Similarity	NPC38350
0.8765	High Similarity	NPC201912
0.875	High Similarity	NPC477371
0.8718	High Similarity	NPC279666
0.8718	High Similarity	NPC192540
0.869	High Similarity	NPC155011
0.8675	High Similarity	NPC472480
0.8675	High Similarity	NPC144258
0.8659	High Similarity	NPC320514
0.8652	High Similarity	NPC477853
0.8605	High Similarity	NPC262043
0.8605	High Similarity	NPC215029
0.8605	High Similarity	NPC476733
0.859	High Similarity	NPC103958
0.859	High Similarity	NPC251970
0.859	High Similarity	NPC161923
0.859	High Similarity	NPC241854
0.859	High Similarity	NPC183503
0.859	High Similarity	NPC283908
0.859	High Similarity	NPC476046
0.8588	High Similarity	NPC136948
0.8588	High Similarity	NPC128644
0.8554	High Similarity	NPC69279
0.8554	High Similarity	NPC83569
0.8554	High Similarity	NPC477373
0.8554	High Similarity	NPC167103
0.8537	High Similarity	NPC477372
0.8519	High Similarity	NPC215843
0.8519	High Similarity	NPC231431
0.8519	High Similarity	NPC158846
0.85	High Similarity	NPC66105
0.8481	Intermediate Similarity	NPC201027
0.8462	Intermediate Similarity	NPC477854
0.8452	Intermediate Similarity	NPC82902
0.8434	Intermediate Similarity	NPC133391
0.8415	Intermediate Similarity	NPC37038
0.8409	Intermediate Similarity	NPC154101
0.8395	Intermediate Similarity	NPC179028
0.8391	Intermediate Similarity	NPC76879
0.8391	Intermediate Similarity	NPC2983
0.8372	Intermediate Similarity	NPC142361
0.8372	Intermediate Similarity	NPC472481
0.8372	Intermediate Similarity	NPC474684
0.8372	Intermediate Similarity	NPC472482
0.8372	Intermediate Similarity	NPC96496
0.8372	Intermediate Similarity	NPC472484
0.8353	Intermediate Similarity	NPC474218
0.8352	Intermediate Similarity	NPC107243
0.8352	Intermediate Similarity	NPC57416
0.8333	Intermediate Similarity	NPC469599
0.8333	Intermediate Similarity	NPC168188
0.8333	Intermediate Similarity	NPC470015
0.8333	Intermediate Similarity	NPC245866
0.8315	Intermediate Similarity	NPC470375
0.8315	Intermediate Similarity	NPC470376
0.8313	Intermediate Similarity	NPC142244
0.8295	Intermediate Similarity	NPC320026
0.8293	Intermediate Similarity	NPC199595
0.8276	Intermediate Similarity	NPC472483
0.8276	Intermediate Similarity	NPC328313
0.8272	Intermediate Similarity	NPC107039
0.8272	Intermediate Similarity	NPC165711
0.8272	Intermediate Similarity	NPC471899
0.8272	Intermediate Similarity	NPC471897
0.8256	Intermediate Similarity	NPC264127
0.8256	Intermediate Similarity	NPC469994
0.8235	Intermediate Similarity	NPC329043
0.8235	Intermediate Similarity	NPC59453
0.8235	Intermediate Similarity	NPC165064
0.8235	Intermediate Similarity	NPC321187
0.8235	Intermediate Similarity	NPC161423
0.8235	Intermediate Similarity	NPC227064
0.8235	Intermediate Similarity	NPC58841
0.8235	Intermediate Similarity	NPC221758
0.8228	Intermediate Similarity	NPC330659
0.8228	Intermediate Similarity	NPC244708
0.8228	Intermediate Similarity	NPC161187
0.8214	Intermediate Similarity	NPC69101
0.8214	Intermediate Similarity	NPC251779
0.8214	Intermediate Similarity	NPC100297
0.8214	Intermediate Similarity	NPC151519
0.8202	Intermediate Similarity	NPC204341
0.8182	Intermediate Similarity	NPC54689
0.8182	Intermediate Similarity	NPC326627
0.8182	Intermediate Similarity	NPC474704
0.8182	Intermediate Similarity	NPC128496
0.8182	Intermediate Similarity	NPC310010
0.8182	Intermediate Similarity	NPC474570
0.8182	Intermediate Similarity	NPC305039
0.8182	Intermediate Similarity	NPC475921
0.8171	Intermediate Similarity	NPC321514
0.8171	Intermediate Similarity	NPC110094
0.8171	Intermediate Similarity	NPC321690
0.8171	Intermediate Similarity	NPC260385
0.8171	Intermediate Similarity	NPC280654
0.8161	Intermediate Similarity	NPC317590
0.8161	Intermediate Similarity	NPC159046
0.8161	Intermediate Similarity	NPC233836
0.8161	Intermediate Similarity	NPC312215
0.8161	Intermediate Similarity	NPC187376
0.8161	Intermediate Similarity	NPC58063
0.8148	Intermediate Similarity	NPC89294
0.8148	Intermediate Similarity	NPC246445
0.8148	Intermediate Similarity	NPC309399
0.814	Intermediate Similarity	NPC123319
0.814	Intermediate Similarity	NPC323765
0.814	Intermediate Similarity	NPC469948
0.814	Intermediate Similarity	NPC94531
0.814	Intermediate Similarity	NPC311702
0.8125	Intermediate Similarity	NPC55527
0.8125	Intermediate Similarity	NPC237591
0.8125	Intermediate Similarity	NPC3753
0.8118	Intermediate Similarity	NPC310470
0.8118	Intermediate Similarity	NPC472492
0.8111	Intermediate Similarity	NPC66429
0.8111	Intermediate Similarity	NPC243866
0.8111	Intermediate Similarity	NPC152897
0.8111	Intermediate Similarity	NPC206810
0.8101	Intermediate Similarity	NPC160817
0.8095	Intermediate Similarity	NPC263272
0.8095	Intermediate Similarity	NPC150506
0.8095	Intermediate Similarity	NPC267691
0.8095	Intermediate Similarity	NPC274050
0.8095	Intermediate Similarity	NPC162632
0.8095	Intermediate Similarity	NPC278459
0.8095	Intermediate Similarity	NPC471898
0.809	Intermediate Similarity	NPC171441
0.809	Intermediate Similarity	NPC471896
0.809	Intermediate Similarity	NPC46281
0.8072	Intermediate Similarity	NPC196827
0.8072	Intermediate Similarity	NPC274996
0.8072	Intermediate Similarity	NPC192744
0.8072	Intermediate Similarity	NPC16394
0.8068	Intermediate Similarity	NPC472220
0.8068	Intermediate Similarity	NPC97884
0.8068	Intermediate Similarity	NPC28227
0.8068	Intermediate Similarity	NPC242864
0.8068	Intermediate Similarity	NPC117122
0.8068	Intermediate Similarity	NPC294480
0.8049	Intermediate Similarity	NPC68828
0.8049	Intermediate Similarity	NPC471035
0.8049	Intermediate Similarity	NPC212661
0.8046	Intermediate Similarity	NPC55309
0.8046	Intermediate Similarity	NPC51014
0.8046	Intermediate Similarity	NPC82979
0.8046	Intermediate Similarity	NPC28252
0.8046	Intermediate Similarity	NPC474778
0.8046	Intermediate Similarity	NPC472869
0.8046	Intermediate Similarity	NPC474733
0.8046	Intermediate Similarity	NPC145879
0.8046	Intermediate Similarity	NPC195640
0.8046	Intermediate Similarity	NPC212843
0.8046	Intermediate Similarity	NPC474732
0.8046	Intermediate Similarity	NPC20688
0.8046	Intermediate Similarity	NPC472479
0.8046	Intermediate Similarity	NPC31564
0.8043	Intermediate Similarity	NPC173272
0.8043	Intermediate Similarity	NPC322063
0.8043	Intermediate Similarity	NPC155676
0.8025	Intermediate Similarity	NPC476844
0.8023	Intermediate Similarity	NPC164577
0.8023	Intermediate Similarity	NPC194937
0.8023	Intermediate Similarity	NPC156981
0.8023	Intermediate Similarity	NPC214043
0.8023	Intermediate Similarity	NPC476038
0.8023	Intermediate Similarity	NPC85774
0.8023	Intermediate Similarity	NPC237712
0.8	Intermediate Similarity	NPC23434
0.8	Intermediate Similarity	NPC189520
0.8	Intermediate Similarity	NPC26888
0.8	Intermediate Similarity	NPC238991
0.8	Intermediate Similarity	NPC170985
0.8	Intermediate Similarity	NPC73882
0.8	Intermediate Similarity	NPC302661
0.7978	Intermediate Similarity	NPC84271
0.7978	Intermediate Similarity	NPC474245
0.7978	Intermediate Similarity	NPC477943
0.7978	Intermediate Similarity	NPC77168
0.7978	Intermediate Similarity	NPC102414
0.7978	Intermediate Similarity	NPC32830
0.7978	Intermediate Similarity	NPC155479
0.7976	Intermediate Similarity	NPC472478
0.7976	Intermediate Similarity	NPC476809
0.7976	Intermediate Similarity	NPC104545
0.7975	Intermediate Similarity	NPC475728
0.7957	Intermediate Similarity	NPC475894
0.7957	Intermediate Similarity	NPC108078
0.7955	Intermediate Similarity	NPC167877
0.7955	Intermediate Similarity	NPC93778
0.7955	Intermediate Similarity	NPC475740
0.7955	Intermediate Similarity	NPC90652
0.7955	Intermediate Similarity	NPC236618
0.7952	Intermediate Similarity	NPC82635
0.7935	Intermediate Similarity	NPC162001

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 NPC477852 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1423
0.2-0.3	4198
0.3-0.4	2273
0.4-0.5	599
0.5-0.6	192
0.6-0.7	137
0.7-0.8	134
0.8-0.85	30
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD4223	Phase 3
0.8889	High Similarity	NPD4221	Approved
0.8675	High Similarity	NPD4197	Approved
0.8621	High Similarity	NPD5284	Approved
0.8621	High Similarity	NPD5281	Approved
0.8571	High Similarity	NPD5329	Approved
0.8471	Intermediate Similarity	NPD6098	Approved
0.8471	Intermediate Similarity	NPD4688	Approved
0.8471	Intermediate Similarity	NPD4693	Phase 3
0.8471	Intermediate Similarity	NPD5690	Phase 2
0.8471	Intermediate Similarity	NPD4689	Approved
0.8471	Intermediate Similarity	NPD4690	Approved
0.8471	Intermediate Similarity	NPD5205	Approved
0.8471	Intermediate Similarity	NPD4138	Approved
0.8354	Intermediate Similarity	NPD4784	Approved
0.8354	Intermediate Similarity	NPD4785	Approved
0.8293	Intermediate Similarity	NPD4195	Approved
0.8276	Intermediate Similarity	NPD5208	Approved
0.8256	Intermediate Similarity	NPD5280	Approved
0.8256	Intermediate Similarity	NPD4694	Approved
0.8235	Intermediate Similarity	NPD4786	Approved
0.8235	Intermediate Similarity	NPD3133	Approved
0.8235	Intermediate Similarity	NPD3665	Phase 1
0.8235	Intermediate Similarity	NPD3666	Approved
0.8214	Intermediate Similarity	NPD3667	Approved
0.8182	Intermediate Similarity	NPD6080	Approved
0.8182	Intermediate Similarity	NPD6673	Approved
0.8182	Intermediate Similarity	NPD4753	Phase 2
0.8182	Intermediate Similarity	NPD6904	Approved
0.8152	Intermediate Similarity	NPD6084	Phase 2
0.8152	Intermediate Similarity	NPD6083	Phase 2
0.8132	Intermediate Similarity	NPD5695	Phase 3
0.8111	Intermediate Similarity	NPD6399	Phase 3
0.8101	Intermediate Similarity	NPD4243	Approved
0.8095	Intermediate Similarity	NPD4692	Approved
0.8095	Intermediate Similarity	NPD4139	Approved
0.809	Intermediate Similarity	NPD5207	Approved
0.8065	Intermediate Similarity	NPD5696	Approved
0.8046	Intermediate Similarity	NPD7146	Approved
0.8046	Intermediate Similarity	NPD5330	Approved
0.8046	Intermediate Similarity	NPD7334	Approved
0.8046	Intermediate Similarity	NPD6684	Approved
0.8046	Intermediate Similarity	NPD7521	Approved
0.8046	Intermediate Similarity	NPD6409	Approved
0.8	Intermediate Similarity	NPD5694	Approved
0.8	Intermediate Similarity	NPD5693	Phase 1
0.7935	Intermediate Similarity	NPD5210	Approved
0.7935	Intermediate Similarity	NPD4629	Approved
0.7912	Intermediate Similarity	NPD4202	Approved
0.7889	Intermediate Similarity	NPD5692	Phase 3
0.7865	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD6903	Approved
0.7865	Intermediate Similarity	NPD4518	Approved
0.7841	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6001	Approved
0.7805	Intermediate Similarity	NPD5275	Approved
0.7805	Intermediate Similarity	NPD4190	Phase 3
0.7802	Intermediate Similarity	NPD6050	Approved
0.7742	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3617	Approved
0.7711	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4788	Approved
0.7692	Intermediate Similarity	NPD4096	Approved
0.7677	Intermediate Similarity	NPD5697	Approved
0.7667	Intermediate Similarity	NPD6672	Approved
0.7667	Intermediate Similarity	NPD5737	Approved
0.764	Intermediate Similarity	NPD3618	Phase 1
0.764	Intermediate Similarity	NPD4623	Approved
0.764	Intermediate Similarity	NPD4519	Discontinued
0.7614	Intermediate Similarity	NPD3668	Phase 3
0.7609	Intermediate Similarity	NPD6079	Approved
0.7604	Intermediate Similarity	NPD5285	Approved
0.7604	Intermediate Similarity	NPD5286	Approved
0.7604	Intermediate Similarity	NPD4696	Approved
0.76	Intermediate Similarity	NPD6011	Approved
0.76	Intermediate Similarity	NPD6881	Approved
0.76	Intermediate Similarity	NPD6899	Approved
0.759	Intermediate Similarity	NPD3702	Approved
0.7582	Intermediate Similarity	NPD5328	Approved
0.7579	Intermediate Similarity	NPD4755	Approved
0.7576	Intermediate Similarity	NPD7128	Approved
0.7576	Intermediate Similarity	NPD5739	Approved
0.7576	Intermediate Similarity	NPD6675	Approved
0.7576	Intermediate Similarity	NPD6402	Approved
0.7558	Intermediate Similarity	NPD4695	Discontinued
0.7531	Intermediate Similarity	NPD4747	Approved
0.7528	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5133	Approved
0.7526	Intermediate Similarity	NPD5223	Approved
0.7525	Intermediate Similarity	NPD6013	Approved
0.7525	Intermediate Similarity	NPD6014	Approved
0.7525	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD5701	Approved
0.7468	Intermediate Similarity	NPD4224	Phase 2
0.7451	Intermediate Similarity	NPD7102	Approved
0.7451	Intermediate Similarity	NPD6883	Approved
0.7451	Intermediate Similarity	NPD7290	Approved
0.7449	Intermediate Similarity	NPD5224	Approved
0.7449	Intermediate Similarity	NPD5211	Phase 2
0.7449	Intermediate Similarity	NPD4633	Approved
0.7449	Intermediate Similarity	NPD5225	Approved
0.7449	Intermediate Similarity	NPD5091	Approved
0.7449	Intermediate Similarity	NPD5226	Approved
0.7444	Intermediate Similarity	NPD5279	Phase 3
0.7426	Intermediate Similarity	NPD7320	Approved
0.7423	Intermediate Similarity	NPD4700	Approved
0.7407	Intermediate Similarity	NPD4137	Phase 3
0.7391	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7339	Approved
0.7381	Intermediate Similarity	NPD6942	Approved
0.7379	Intermediate Similarity	NPD6650	Approved
0.7379	Intermediate Similarity	NPD6617	Approved
0.7379	Intermediate Similarity	NPD6869	Approved
0.7379	Intermediate Similarity	NPD6649	Approved
0.7379	Intermediate Similarity	NPD6847	Approved
0.7379	Intermediate Similarity	NPD8130	Phase 1
0.7374	Intermediate Similarity	NPD5175	Approved
0.7374	Intermediate Similarity	NPD5174	Approved
0.7368	Intermediate Similarity	NPD5654	Approved
0.7363	Intermediate Similarity	NPD3573	Approved
0.7353	Intermediate Similarity	NPD6373	Approved
0.7353	Intermediate Similarity	NPD6372	Approved
0.7317	Intermediate Similarity	NPD4691	Approved
0.7308	Intermediate Similarity	NPD6882	Approved
0.7308	Intermediate Similarity	NPD8297	Approved
0.73	Intermediate Similarity	NPD5141	Approved
0.7292	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5369	Approved
0.7262	Intermediate Similarity	NPD4058	Approved
0.7262	Intermediate Similarity	NPD4687	Approved
0.7238	Intermediate Similarity	NPD4632	Approved
0.7234	Intermediate Similarity	NPD7515	Phase 2
0.7229	Intermediate Similarity	NPD6081	Approved
0.7228	Intermediate Similarity	NPD6008	Approved
0.7216	Intermediate Similarity	NPD5959	Approved
0.7216	Intermediate Similarity	NPD5173	Approved
0.7212	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6051	Approved
0.72	Intermediate Similarity	NPD6052	Approved
0.72	Intermediate Similarity	NPD4754	Approved
0.7174	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6614	Approved
0.7126	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4697	Phase 3
0.7111	Intermediate Similarity	NPD5362	Discontinued
0.7087	Intermediate Similarity	NPD4730	Approved
0.7087	Intermediate Similarity	NPD4729	Approved
0.7083	Intermediate Similarity	NPD5707	Approved
0.7083	Intermediate Similarity	NPD7748	Approved
0.7073	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5360	Phase 3
0.7071	Intermediate Similarity	NPD6404	Discontinued
0.7059	Intermediate Similarity	NPD4767	Approved
0.7059	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD6924	Approved
0.7059	Intermediate Similarity	NPD6926	Approved
0.7059	Intermediate Similarity	NPD5733	Approved
0.7059	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD8035	Phase 2
0.7053	Intermediate Similarity	NPD8034	Phase 2
0.7037	Intermediate Similarity	NPD6009	Approved
0.7037	Intermediate Similarity	NPD6317	Approved
0.7024	Intermediate Similarity	NPD5276	Approved
0.7	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD4270	Approved
0.6988	Remote Similarity	NPD3698	Phase 2
0.6972	Remote Similarity	NPD6314	Approved
0.6972	Remote Similarity	NPD6335	Approved
0.6972	Remote Similarity	NPD6313	Approved
0.697	Remote Similarity	NPD7638	Approved
0.6966	Remote Similarity	NPD4748	Discontinued
0.6966	Remote Similarity	NPD4822	Approved
0.6966	Remote Similarity	NPD4821	Approved
0.6966	Remote Similarity	NPD7525	Registered
0.6966	Remote Similarity	NPD4820	Approved
0.6966	Remote Similarity	NPD4819	Approved
0.6966	Remote Similarity	NPD5368	Approved
0.6952	Remote Similarity	NPD5251	Approved
0.6952	Remote Similarity	NPD4634	Approved
0.6952	Remote Similarity	NPD5250	Approved
0.6952	Remote Similarity	NPD5249	Phase 3
0.6952	Remote Similarity	NPD5248	Approved
0.6952	Remote Similarity	NPD5169	Approved
0.6952	Remote Similarity	NPD5247	Approved
0.6952	Remote Similarity	NPD5135	Approved
0.6952	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6274	Approved
0.6923	Remote Similarity	NPD5128	Approved
0.6915	Remote Similarity	NPD4722	Approved
0.6915	Remote Similarity	NPD4723	Approved
0.6914	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7100	Approved
0.6909	Remote Similarity	NPD7101	Approved
0.6905	Remote Similarity	NPD4245	Approved
0.6905	Remote Similarity	NPD4244	Approved
0.69	Remote Similarity	NPD7640	Approved
0.69	Remote Similarity	NPD7639	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