NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	517.591
LogP:	6.275
LogD:	5.419
LogS:	-5.603
# Rotatable Bonds:	9
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	4.738
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.931
MDCK Permeability:	1.8083668692270294e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.123

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	96.4055404663086%
Volume Distribution (VD):	0.587
Pgp-substrate:	3.160304546356201%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.316
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.32
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.614
CYP3A4-inhibitor:	0.276
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	4.307
Half-life (T1/2):	0.351

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.46
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.185
Skin Sensitization:	0.165
Carcinogencity:	0.084
Eye Corrosion:	0.038
Eye Irritation:	0.089
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC477371

Natural Product ID:	NPC477371
*Common Name:**	3-[(3R,3aR,5aR,6S,7S,9bR)-3a,6,9b-trimethyl-3-[(2R)-6-methyl-4-oxoheptan-2-yl]-7-prop-1-en-2-yl-1,2,3,4,5,5a,7,8-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
IUPAC Name:	3-[(3R,3aR,5aR,6S,7S,9bR)-3a,6,9b-trimethyl-3-[(2R)-6-methyl-4-oxoheptan-2-yl]-7-prop-1-en-2-yl-1,2,3,4,5,5a,7,8-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
Synonyms:
Standard InCHIKey:	WILCWEDZNDPYTR-IYCLCXJYSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-19(2)17-22(31)18-21(5)24-11-15-30(8)26-10-9-23(20(3)4)28(6,14-13-27(32)33)25(26)12-16-29(24,30)7/h10,19,21,23-25H,3,9,11-18H2,1-2,4-8H3,(H,32,33)/t21-,23+,24-,25+,28+,29-,30+/m1/s1
SMILES:	C[C@H](CC(=O)CC(C)C)[C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC[C@H]([C@]3(C)CCC(=O)O)C(=C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44586014
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18027905]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271558]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	roots	n.a.	n.a.	PMID[18491866]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590312]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24299567]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214125]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[27704807]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO912	Kadsura coccinea	Species	Schisandraceae	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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	6800	nM	PMID[18491866]

☑ 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 NPC477371 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	135
0.1-0.2	1020
0.2-0.3	6342
0.3-0.4	15511
0.4-0.5	7007
0.5-0.6	6644
0.6-0.7	4282
0.7-0.8	1488
0.8-0.85	212
0.85-0.9	40
0.9-0.95	10
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC201912
0.9733	High Similarity	NPC38350
0.9733	High Similarity	NPC147066
0.9733	High Similarity	NPC477372
0.9605	High Similarity	NPC260956
0.9605	High Similarity	NPC133391
0.9481	High Similarity	NPC69279
0.9481	High Similarity	NPC83569
0.9481	High Similarity	NPC477373
0.9351	High Similarity	NPC320514
0.9241	High Similarity	NPC29447
0.9211	High Similarity	NPC158846
0.9114	High Similarity	NPC165064
0.9041	High Similarity	NPC160817
0.9012	High Similarity	NPC96496
0.9012	High Similarity	NPC136948
0.8987	High Similarity	NPC168188
0.8987	High Similarity	NPC470015
0.8961	High Similarity	NPC274996
0.8961	High Similarity	NPC196827
0.8961	High Similarity	NPC215843
0.8889	High Similarity	NPC155011
0.8875	High Similarity	NPC164577
0.8861	High Similarity	NPC240302
0.8831	High Similarity	NPC179028
0.8831	High Similarity	NPC321514
0.8816	High Similarity	NPC180886
0.8816	High Similarity	NPC20466
0.8795	High Similarity	NPC262043
0.8795	High Similarity	NPC474570
0.878	High Similarity	NPC167877
0.878	High Similarity	NPC159046
0.878	High Similarity	NPC187376
0.878	High Similarity	NPC142361
0.878	High Similarity	NPC233836
0.878	High Similarity	NPC474684
0.8765	High Similarity	NPC311702
0.8765	High Similarity	NPC269638
0.8765	High Similarity	NPC94531
0.8765	High Similarity	NPC123319
0.875	High Similarity	NPC477852
0.875	High Similarity	NPC310470
0.875	High Similarity	NPC97913
0.875	High Similarity	NPC167103
0.8734	High Similarity	NPC278459
0.8734	High Similarity	NPC267691
0.8734	High Similarity	NPC162632
0.8734	High Similarity	NPC471898
0.8734	High Similarity	NPC263272
0.8734	High Similarity	NPC274050
0.8718	High Similarity	NPC231431
0.8718	High Similarity	NPC192744
0.8701	High Similarity	NPC66105
0.8701	High Similarity	NPC107039
0.8701	High Similarity	NPC471897
0.8701	High Similarity	NPC165711
0.8701	High Similarity	NPC471899
0.8684	High Similarity	NPC192540
0.8684	High Similarity	NPC279666
0.8659	High Similarity	NPC28252
0.8659	High Similarity	NPC55309
0.8642	High Similarity	NPC214043
0.8642	High Similarity	NPC476038
0.8642	High Similarity	NPC194937
0.8642	High Similarity	NPC472865
0.8642	High Similarity	NPC85774
0.8642	High Similarity	NPC82902
0.8642	High Similarity	NPC473246
0.8642	High Similarity	NPC221758
0.8642	High Similarity	NPC59453
0.8625	High Similarity	NPC296367
0.8625	High Similarity	NPC251779
0.8625	High Similarity	NPC193347
0.8625	High Similarity	NPC69101
0.8608	High Similarity	NPC37038
0.859	High Similarity	NPC110094
0.859	High Similarity	NPC74410
0.859	High Similarity	NPC321690
0.859	High Similarity	NPC260385
0.859	High Similarity	NPC280654
0.8588	High Similarity	NPC204341
0.8588	High Similarity	NPC154101
0.8571	High Similarity	NPC89294
0.8571	High Similarity	NPC84271
0.8571	High Similarity	NPC246445
0.8571	High Similarity	NPC474704
0.8571	High Similarity	NPC77168
0.8571	High Similarity	NPC69143
0.8571	High Similarity	NPC309399
0.8571	High Similarity	NPC102414
0.8571	High Similarity	NPC54689
0.8571	High Similarity	NPC475921
0.8554	High Similarity	NPC128644
0.8554	High Similarity	NPC312215
0.8553	High Similarity	NPC241854
0.8553	High Similarity	NPC283908
0.8553	High Similarity	NPC183503
0.8553	High Similarity	NPC251970
0.8553	High Similarity	NPC301065
0.8553	High Similarity	NPC103958
0.8553	High Similarity	NPC161923
0.8553	High Similarity	NPC476046
0.8537	High Similarity	NPC142649
0.8537	High Similarity	NPC470223
0.8537	High Similarity	NPC474083
0.8537	High Similarity	NPC283733
0.8537	High Similarity	NPC11711
0.8537	High Similarity	NPC474218
0.8537	High Similarity	NPC469948
0.8537	High Similarity	NPC473038
0.8537	High Similarity	NPC471224
0.8519	High Similarity	NPC70834
0.8519	High Similarity	NPC476082
0.8519	High Similarity	NPC278648
0.85	High Similarity	NPC327002
0.85	High Similarity	NPC142244
0.8488	Intermediate Similarity	NPC152897
0.8488	Intermediate Similarity	NPC66429
0.8481	Intermediate Similarity	NPC16394
0.8481	Intermediate Similarity	NPC199595
0.8481	Intermediate Similarity	NPC327674
0.8471	Intermediate Similarity	NPC175628
0.8471	Intermediate Similarity	NPC471896
0.8471	Intermediate Similarity	NPC111585
0.8471	Intermediate Similarity	NPC148414
0.8462	Intermediate Similarity	NPC471035
0.8462	Intermediate Similarity	NPC212661
0.8462	Intermediate Similarity	NPC97377
0.8462	Intermediate Similarity	NPC68828
0.8452	Intermediate Similarity	NPC294480
0.8452	Intermediate Similarity	NPC242864
0.8452	Intermediate Similarity	NPC117122
0.8442	Intermediate Similarity	NPC476844
0.8442	Intermediate Similarity	NPC476795
0.8434	Intermediate Similarity	NPC212843
0.8434	Intermediate Similarity	NPC51014
0.8434	Intermediate Similarity	NPC31564
0.8434	Intermediate Similarity	NPC474732
0.8434	Intermediate Similarity	NPC474778
0.8434	Intermediate Similarity	NPC145879
0.8434	Intermediate Similarity	NPC6247
0.8434	Intermediate Similarity	NPC474733
0.8434	Intermediate Similarity	NPC186975
0.8434	Intermediate Similarity	NPC469994
0.8434	Intermediate Similarity	NPC472869
0.8421	Intermediate Similarity	NPC244708
0.8421	Intermediate Similarity	NPC330659
0.8421	Intermediate Similarity	NPC161187
0.8415	Intermediate Similarity	NPC237712
0.8415	Intermediate Similarity	NPC19849
0.8415	Intermediate Similarity	NPC144258
0.8415	Intermediate Similarity	NPC96095
0.8415	Intermediate Similarity	NPC472864
0.8415	Intermediate Similarity	NPC209882
0.8415	Intermediate Similarity	NPC100391
0.8395	Intermediate Similarity	NPC321289
0.8395	Intermediate Similarity	NPC151519
0.8395	Intermediate Similarity	NPC142253
0.8395	Intermediate Similarity	NPC327969
0.8395	Intermediate Similarity	NPC3511
0.8395	Intermediate Similarity	NPC100297
0.8395	Intermediate Similarity	NPC472239
0.8375	Intermediate Similarity	NPC104545
0.8375	Intermediate Similarity	NPC472478
0.8372	Intermediate Similarity	NPC189520
0.8372	Intermediate Similarity	NPC86266
0.8372	Intermediate Similarity	NPC212301
0.8372	Intermediate Similarity	NPC110657
0.8372	Intermediate Similarity	NPC297265
0.8372	Intermediate Similarity	NPC26888
0.8354	Intermediate Similarity	NPC471409
0.8354	Intermediate Similarity	NPC275494
0.8354	Intermediate Similarity	NPC82635
0.8353	Intermediate Similarity	NPC474889
0.8353	Intermediate Similarity	NPC476733
0.8353	Intermediate Similarity	NPC215029
0.8353	Intermediate Similarity	NPC128496
0.8353	Intermediate Similarity	NPC214387
0.8333	Intermediate Similarity	NPC317590
0.8333	Intermediate Similarity	NPC93778
0.8333	Intermediate Similarity	NPC58063
0.8333	Intermediate Similarity	NPC236618
0.8333	Intermediate Similarity	NPC90652
0.8333	Intermediate Similarity	NPC475740
0.8313	Intermediate Similarity	NPC202868
0.8313	Intermediate Similarity	NPC474537
0.8312	Intermediate Similarity	NPC237591
0.8312	Intermediate Similarity	NPC3753
0.8295	Intermediate Similarity	NPC171395
0.8295	Intermediate Similarity	NPC263347
0.8295	Intermediate Similarity	NPC469599
0.8293	Intermediate Similarity	NPC472740
0.8276	Intermediate Similarity	NPC107674
0.8276	Intermediate Similarity	NPC170220
0.8276	Intermediate Similarity	NPC206810
0.8276	Intermediate Similarity	NPC243866
0.8276	Intermediate Similarity	NPC470376
0.8276	Intermediate Similarity	NPC141497
0.8276	Intermediate Similarity	NPC470375
0.8276	Intermediate Similarity	NPC470224

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 NPC477371 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	1496
0.2-0.3	4169
0.3-0.4	2217
0.4-0.5	619
0.5-0.6	208
0.6-0.7	171
0.7-0.8	104
0.8-0.85	32
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD4786	Approved
0.8625	High Similarity	NPD4223	Phase 3
0.8625	High Similarity	NPD4221	Approved
0.8537	High Similarity	NPD5329	Approved
0.8488	Intermediate Similarity	NPD6399	Phase 3
0.8434	Intermediate Similarity	NPD6098	Approved
0.8415	Intermediate Similarity	NPD4197	Approved
0.8395	Intermediate Similarity	NPD3667	Approved
0.8372	Intermediate Similarity	NPD5284	Approved
0.8372	Intermediate Similarity	NPD5281	Approved
0.8235	Intermediate Similarity	NPD5737	Approved
0.8235	Intermediate Similarity	NPD6672	Approved
0.8214	Intermediate Similarity	NPD4688	Approved
0.8214	Intermediate Similarity	NPD5205	Approved
0.8214	Intermediate Similarity	NPD5330	Approved
0.8214	Intermediate Similarity	NPD5690	Phase 2
0.8214	Intermediate Similarity	NPD7146	Approved
0.8214	Intermediate Similarity	NPD7334	Approved
0.8214	Intermediate Similarity	NPD4138	Approved
0.8214	Intermediate Similarity	NPD4694	Approved
0.8214	Intermediate Similarity	NPD5280	Approved
0.8214	Intermediate Similarity	NPD4689	Approved
0.8214	Intermediate Similarity	NPD6684	Approved
0.8214	Intermediate Similarity	NPD4690	Approved
0.8214	Intermediate Similarity	NPD7521	Approved
0.8214	Intermediate Similarity	NPD6409	Approved
0.8214	Intermediate Similarity	NPD4693	Phase 3
0.8193	Intermediate Similarity	NPD3666	Approved
0.8193	Intermediate Similarity	NPD3665	Phase 1
0.8193	Intermediate Similarity	NPD3133	Approved
0.814	Intermediate Similarity	NPD6673	Approved
0.814	Intermediate Similarity	NPD5328	Approved
0.814	Intermediate Similarity	NPD6080	Approved
0.814	Intermediate Similarity	NPD6904	Approved
0.8125	Intermediate Similarity	NPD3617	Approved
0.8111	Intermediate Similarity	NPD6084	Phase 2
0.8111	Intermediate Similarity	NPD6083	Phase 2
0.809	Intermediate Similarity	NPD5695	Phase 3
0.8049	Intermediate Similarity	NPD4139	Approved
0.8049	Intermediate Similarity	NPD4692	Approved
0.8023	Intermediate Similarity	NPD5208	Approved
0.8023	Intermediate Similarity	NPD6903	Approved
0.8023	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD5279	Phase 3
0.7955	Intermediate Similarity	NPD6079	Approved
0.7955	Intermediate Similarity	NPD6050	Approved
0.7931	Intermediate Similarity	NPD4753	Phase 2
0.7922	Intermediate Similarity	NPD4747	Approved
0.7882	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5733	Approved
0.7841	Intermediate Similarity	NPD5692	Phase 3
0.7841	Intermediate Similarity	NPD5207	Approved
0.7826	Intermediate Similarity	NPD5696	Approved
0.7821	Intermediate Similarity	NPD4243	Approved
0.7805	Intermediate Similarity	NPD4195	Approved
0.7792	Intermediate Similarity	NPD4137	Phase 3
0.7791	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3668	Phase 3
0.7753	Intermediate Similarity	NPD7515	Phase 2
0.7753	Intermediate Similarity	NPD5694	Approved
0.7753	Intermediate Similarity	NPD5693	Phase 1
0.7727	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4695	Discontinued
0.7692	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4691	Approved
0.7683	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4202	Approved
0.7662	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4788	Approved
0.764	Intermediate Similarity	NPD4096	Approved
0.7632	Intermediate Similarity	NPD4224	Phase 2
0.7625	Intermediate Similarity	NPD4785	Approved
0.7625	Intermediate Similarity	NPD4784	Approved
0.7625	Intermediate Similarity	NPD4687	Approved
0.7595	Intermediate Similarity	NPD5276	Approved
0.7595	Intermediate Similarity	NPD6081	Approved
0.7586	Intermediate Similarity	NPD4623	Approved
0.7586	Intermediate Similarity	NPD4519	Discontinued
0.7582	Intermediate Similarity	NPD7748	Approved
0.7582	Intermediate Similarity	NPD6001	Approved
0.7553	Intermediate Similarity	NPD6404	Discontinued
0.7531	Intermediate Similarity	NPD6942	Approved
0.7531	Intermediate Similarity	NPD7339	Approved
0.7526	Intermediate Similarity	NPD7128	Approved
0.7526	Intermediate Similarity	NPD6402	Approved
0.7526	Intermediate Similarity	NPD5739	Approved
0.7526	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD5210	Approved
0.7473	Intermediate Similarity	NPD5133	Approved
0.7419	Intermediate Similarity	NPD5222	Approved
0.7419	Intermediate Similarity	NPD5221	Approved
0.7419	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4697	Phase 3
0.7416	Intermediate Similarity	NPD4518	Approved
0.7407	Intermediate Similarity	NPD4058	Approved
0.7374	Intermediate Similarity	NPD6881	Approved
0.7374	Intermediate Similarity	NPD6899	Approved
0.7374	Intermediate Similarity	NPD7320	Approved
0.7363	Intermediate Similarity	NPD8034	Phase 2
0.7363	Intermediate Similarity	NPD8035	Phase 2
0.734	Intermediate Similarity	NPD5173	Approved
0.734	Intermediate Similarity	NPD4755	Approved
0.734	Intermediate Similarity	NPD7902	Approved
0.7317	Intermediate Similarity	NPD4190	Phase 3
0.7317	Intermediate Similarity	NPD5275	Approved
0.7312	Intermediate Similarity	NPD5654	Approved
0.7303	Intermediate Similarity	NPD3573	Approved
0.73	Intermediate Similarity	NPD6373	Approved
0.73	Intermediate Similarity	NPD6372	Approved
0.7273	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5697	Approved
0.7273	Intermediate Similarity	NPD5701	Approved
0.7234	Intermediate Similarity	NPD7614	Phase 1
0.7229	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6883	Approved
0.7228	Intermediate Similarity	NPD7102	Approved
0.7228	Intermediate Similarity	NPD7290	Approved
0.7215	Intermediate Similarity	NPD5360	Phase 3
0.7215	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6011	Approved
0.7195	Intermediate Similarity	NPD6924	Approved
0.7195	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6926	Approved
0.7188	Intermediate Similarity	NPD5286	Approved
0.7188	Intermediate Similarity	NPD5285	Approved
0.7188	Intermediate Similarity	NPD4700	Approved
0.7188	Intermediate Similarity	NPD4696	Approved
0.7179	Intermediate Similarity	NPD7331	Phase 2
0.7158	Intermediate Similarity	NPD5959	Approved
0.7157	Intermediate Similarity	NPD8130	Phase 1
0.7157	Intermediate Similarity	NPD6650	Approved
0.7157	Intermediate Similarity	NPD6617	Approved
0.7157	Intermediate Similarity	NPD6869	Approved
0.7157	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6649	Approved
0.7157	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6052	Approved
0.7129	Intermediate Similarity	NPD6014	Approved
0.7129	Intermediate Similarity	NPD6012	Approved
0.7129	Intermediate Similarity	NPD6013	Approved
0.7126	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5223	Approved
0.7093	Intermediate Similarity	NPD5368	Approved
0.7093	Intermediate Similarity	NPD7525	Registered
0.7087	Intermediate Similarity	NPD8297	Approved
0.7087	Intermediate Similarity	NPD6882	Approved
0.7083	Intermediate Similarity	NPD7638	Approved
0.7051	Intermediate Similarity	NPD7341	Phase 2
0.7045	Intermediate Similarity	NPD5362	Discontinued
0.7041	Intermediate Similarity	NPD4633	Approved
0.7041	Intermediate Similarity	NPD5091	Approved
0.7041	Intermediate Similarity	NPD5226	Approved
0.7041	Intermediate Similarity	NPD5224	Approved
0.7041	Intermediate Similarity	NPD5211	Phase 2
0.7041	Intermediate Similarity	NPD5225	Approved
0.7037	Intermediate Similarity	NPD4789	Approved
0.7024	Intermediate Similarity	NPD6933	Approved
0.7024	Intermediate Similarity	NPD6117	Approved
0.7021	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7900	Approved
0.7011	Intermediate Similarity	NPD5369	Approved
0.701	Intermediate Similarity	NPD7639	Approved
0.701	Intermediate Similarity	NPD7640	Approved
0.6989	Remote Similarity	NPD6411	Approved
0.697	Remote Similarity	NPD5174	Approved
0.697	Remote Similarity	NPD5175	Approved
0.697	Remote Similarity	NPD4754	Approved
0.6957	Remote Similarity	NPD6051	Approved
0.6951	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6116	Phase 1
0.6932	Remote Similarity	NPD6435	Approved
0.6932	Remote Similarity	NPD4269	Approved
0.6932	Remote Similarity	NPD4270	Approved
0.6931	Remote Similarity	NPD6614	Approved
0.6931	Remote Similarity	NPD6412	Phase 2
0.6914	Remote Similarity	NPD6923	Approved
0.6914	Remote Similarity	NPD6922	Approved
0.6905	Remote Similarity	NPD3702	Approved
0.69	Remote Similarity	NPD5141	Approved
0.6889	Remote Similarity	NPD1694	Approved
0.6887	Remote Similarity	NPD6868	Approved
0.686	Remote Similarity	NPD6115	Approved
0.686	Remote Similarity	NPD6118	Approved
0.686	Remote Similarity	NPD6697	Approved
0.686	Remote Similarity	NPD6114	Approved
0.6857	Remote Similarity	NPD4632	Approved
0.6832	Remote Similarity	NPD4768	Approved
0.6832	Remote Similarity	NPD6008	Approved
0.6832	Remote Similarity	NPD4767	Approved
0.6829	Remote Similarity	NPD4245	Approved
0.6829	Remote Similarity	NPD7144	Approved
0.6829	Remote Similarity	NPD4244	Approved
0.6829	Remote Similarity	NPD7143	Approved
0.6822	Remote Similarity	NPD7115	Discovery
0.6818	Remote Similarity	NPD857	Phase 3
0.6809	Remote Similarity	NPD7637	Suspended
0.6782	Remote Similarity	NPD6929	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