NPASS Compound

Structure

NPC34019 OpenBabel07101718282D 30 34 0 0 1 0 0 0 0 0999 V2000 6.4325 5.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6915 1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7436 3.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1235 4.1270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0005 2.4057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7926 3.3838 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 21 2 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 1 1 1 0 0 0 19 2 1 6 0 0 0 19 25 1 0 0 0 0 20 3 1 1 0 0 0 20 24 1 0 0 0 0 21 28 1 0 0 0 0 22 30 1 1 0 0 0 23 9 1 6 0 0 0 23 26 1 0 0 0 0 23 27 1 0 0 0 0 24 18 1 6 0 0 0 25 29 1 1 0 0 0 26 29 1 1 0 0 0 27 28 1 1 0 0 0 28 4 1 1 0 0 0 29 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.37
Volume:	473.512
LogP:	7.859
LogD:	6.914
LogS:	-6.726
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	4.583
Fsp3:	0.931
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:	-4.701
MDCK Permeability:	1.110042467189487e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.417
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.067

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.17
Plasma Protein Binding (PPB):	93.11500549316406%
Volume Distribution (VD):	1.517
Pgp-substrate:	1.0428460836410522%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.601
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.181
CYP2C9-substrate:	0.176
CYP2D6-inhibitor:	0.089
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.617
CYP3A4-substrate:	0.674

ADMET: Excretion

Clearance (CL):	7.898
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.986
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.753
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.258
Skin Sensitization:	0.968
Carcinogencity:	0.139
Eye Corrosion:	0.907
Eye Irritation:	0.569
Respiratory Toxicity:	0.544

Download Data

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

Natural Product: NPC34019

Natural Product ID:	NPC34019
*Common Name:**	Petrosterol
IUPAC Name:	(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R,5R)-5-[(1R,2R)-2-methylcyclopropyl]hexan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:	Petrosterol
Standard InCHIKey:	AOOVLQXWRHMRMX-BFPAFGTMSA-N
Standard InCHI:	InChI=1S/C29H48O/c1-18(24-16-20(24)3)6-7-19(2)25-10-11-26-23-9-8-21-17-22(30)12-14-28(21,4)27(23)13-15-29(25,26)5/h8,18-20,22-27,30H,6-7,9-17H2,1-5H3/t18-,19-,20-,22+,23+,24+,25-,26+,27+,28+,29-/m1/s1
SMILES:	O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CC[C@H]([C@@H]2C[C@H]2C)C)C)C)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559744
PubChem CID:	194249
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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
NPO32556	Ianthella sp.	Species	Thorectidae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19615900]
NPO32556	Ianthella sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8254355]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6
Others	3

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	52.58	%	PMID[533833]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	27.4	%	PMID[533833]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	12.61	%	PMID[533833]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	18700.0	nM	PMID[533833]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	19800.0	nM	PMID[533833]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16400.0	nM	PMID[533833]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	46500.0	nM	PMID[533833]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	21500.0	nM	PMID[533833]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	11500.0	nM	PMID[533833]

☑ 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 NPC34019 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	170
0.1-0.2	1530
0.2-0.3	9199
0.3-0.4	14947
0.4-0.5	6512
0.5-0.6	5741
0.6-0.7	3530
0.7-0.8	834
0.8-0.85	128
0.85-0.9	64
0.9-0.95	41
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC134847
0.9718	High Similarity	NPC230301
0.9718	High Similarity	NPC136188
0.9718	High Similarity	NPC285893
0.9718	High Similarity	NPC28657
0.9718	High Similarity	NPC304309
0.9718	High Similarity	NPC22105
0.9718	High Similarity	NPC162742
0.9718	High Similarity	NPC288035
0.9583	High Similarity	NPC321016
0.9583	High Similarity	NPC300324
0.9583	High Similarity	NPC107059
0.9583	High Similarity	NPC113733
0.9583	High Similarity	NPC240604
0.9583	High Similarity	NPC321381
0.9452	High Similarity	NPC198968
0.9452	High Similarity	NPC155986
0.9452	High Similarity	NPC318495
0.9444	High Similarity	NPC471723
0.9444	High Similarity	NPC141071
0.9444	High Similarity	NPC257347
0.9324	High Similarity	NPC307965
0.9324	High Similarity	NPC302041
0.9324	High Similarity	NPC473943
0.9324	High Similarity	NPC85346
0.9324	High Similarity	NPC87604
0.9324	High Similarity	NPC18603
0.9324	High Similarity	NPC65897
0.9324	High Similarity	NPC477522
0.9324	High Similarity	NPC474216
0.9324	High Similarity	NPC76931
0.9315	High Similarity	NPC129165
0.9315	High Similarity	NPC134330
0.9315	High Similarity	NPC189883
0.92	High Similarity	NPC328714
0.92	High Similarity	NPC28862
0.92	High Similarity	NPC109546
0.92	High Similarity	NPC81306
0.92	High Similarity	NPC47982
0.92	High Similarity	NPC143182
0.92	High Similarity	NPC84694
0.9079	High Similarity	NPC164840
0.9079	High Similarity	NPC241290
0.9079	High Similarity	NPC234193
0.9079	High Similarity	NPC209944
0.9079	High Similarity	NPC26117
0.9067	High Similarity	NPC312328
0.9067	High Similarity	NPC275910
0.9054	High Similarity	NPC247325
0.9054	High Similarity	NPC202642
0.9054	High Similarity	NPC470362
0.9054	High Similarity	NPC96319
0.9054	High Similarity	NPC237460
0.9054	High Similarity	NPC46160
0.9054	High Similarity	NPC244488
0.8974	High Similarity	NPC475789
0.8961	High Similarity	NPC474531
0.8961	High Similarity	NPC264245
0.8961	High Similarity	NPC47761
0.8961	High Similarity	NPC474752
0.8961	High Similarity	NPC209620
0.8961	High Similarity	NPC474759
0.8961	High Similarity	NPC23852
0.8961	High Similarity	NPC474731
0.8961	High Similarity	NPC470383
0.8961	High Similarity	NPC474683
0.8961	High Similarity	NPC82986
0.8961	High Similarity	NPC7505
0.8947	High Similarity	NPC30986
0.8947	High Similarity	NPC209430
0.8947	High Similarity	NPC1319
0.8933	High Similarity	NPC214570
0.8919	High Similarity	NPC322353
0.8919	High Similarity	NPC121744
0.8919	High Similarity	NPC118508
0.8904	High Similarity	NPC195489
0.8904	High Similarity	NPC471799
0.8904	High Similarity	NPC474140
0.8875	High Similarity	NPC94462
0.8873	High Similarity	NPC208999
0.8873	High Similarity	NPC160209
0.8846	High Similarity	NPC1272
0.8846	High Similarity	NPC189972
0.8846	High Similarity	NPC470614
0.8846	High Similarity	NPC5985
0.8846	High Similarity	NPC50964
0.8846	High Similarity	NPC101462
0.8846	High Similarity	NPC49964
0.8831	High Similarity	NPC236112
0.8816	High Similarity	NPC285761
0.8816	High Similarity	NPC167037
0.8816	High Similarity	NPC205455
0.8816	High Similarity	NPC6978
0.8816	High Similarity	NPC138621
0.8816	High Similarity	NPC244385
0.8816	High Similarity	NPC477514
0.8816	High Similarity	NPC186191
0.88	High Similarity	NPC73875
0.8784	High Similarity	NPC145552
0.8784	High Similarity	NPC254509
0.8784	High Similarity	NPC471797
0.8784	High Similarity	NPC469534
0.8784	High Similarity	NPC196358
0.8784	High Similarity	NPC469533
0.8784	High Similarity	NPC49168
0.8784	High Similarity	NPC469593
0.8784	High Similarity	NPC5046
0.875	High Similarity	NPC474189
0.875	High Similarity	NPC474349
0.8734	High Similarity	NPC317458
0.8734	High Similarity	NPC113978
0.8734	High Similarity	NPC474634
0.8701	High Similarity	NPC273410
0.8701	High Similarity	NPC80530
0.8667	High Similarity	NPC200243
0.8667	High Similarity	NPC230704
0.8667	High Similarity	NPC471468
0.8667	High Similarity	NPC70982
0.8649	High Similarity	NPC201373
0.8649	High Similarity	NPC182717
0.863	High Similarity	NPC475728
0.863	High Similarity	NPC145498
0.8625	High Similarity	NPC33913
0.8625	High Similarity	NPC472265
0.8625	High Similarity	NPC221758
0.8625	High Similarity	NPC185568
0.8625	High Similarity	NPC205845
0.8625	High Similarity	NPC124172
0.8625	High Similarity	NPC209802
0.8625	High Similarity	NPC59453
0.8625	High Similarity	NPC474047
0.8608	High Similarity	NPC30166
0.8608	High Similarity	NPC248886
0.8608	High Similarity	NPC470049
0.8608	High Similarity	NPC201852
0.859	High Similarity	NPC13554
0.859	High Similarity	NPC102253
0.859	High Similarity	NPC322313
0.859	High Similarity	NPC236237
0.8571	High Similarity	NPC318136
0.8553	High Similarity	NPC106364
0.8533	High Similarity	NPC329090
0.8533	High Similarity	NPC27395
0.8533	High Similarity	NPC477138
0.8533	High Similarity	NPC100334
0.8533	High Similarity	NPC243342
0.8519	High Similarity	NPC157257
0.8519	High Similarity	NPC274448
0.8519	High Similarity	NPC266511
0.8514	High Similarity	NPC242001
0.8514	High Similarity	NPC111234
0.85	High Similarity	NPC82623
0.85	High Similarity	NPC134481
0.8493	Intermediate Similarity	NPC167272
0.8493	Intermediate Similarity	NPC269877
0.8472	Intermediate Similarity	NPC197805
0.8462	Intermediate Similarity	NPC472463
0.8442	Intermediate Similarity	NPC257191
0.8442	Intermediate Similarity	NPC471798
0.8442	Intermediate Similarity	NPC331618
0.8434	Intermediate Similarity	NPC67872
0.8421	Intermediate Similarity	NPC291503
0.8421	Intermediate Similarity	NPC328104
0.8421	Intermediate Similarity	NPC477923
0.8421	Intermediate Similarity	NPC66566
0.8421	Intermediate Similarity	NPC319090
0.8415	Intermediate Similarity	NPC51014
0.8415	Intermediate Similarity	NPC31564
0.8415	Intermediate Similarity	NPC474732
0.8415	Intermediate Similarity	NPC145879
0.8415	Intermediate Similarity	NPC474733
0.8415	Intermediate Similarity	NPC474778
0.8415	Intermediate Similarity	NPC6391
0.8415	Intermediate Similarity	NPC477604
0.8415	Intermediate Similarity	NPC24277
0.8415	Intermediate Similarity	NPC125399
0.8415	Intermediate Similarity	NPC293287
0.8415	Intermediate Similarity	NPC152808
0.8415	Intermediate Similarity	NPC155011
0.8415	Intermediate Similarity	NPC474970
0.8415	Intermediate Similarity	NPC71520
0.8415	Intermediate Similarity	NPC261266
0.8415	Intermediate Similarity	NPC269058
0.8395	Intermediate Similarity	NPC470077
0.8395	Intermediate Similarity	NPC478102
0.8395	Intermediate Similarity	NPC238485
0.8378	Intermediate Similarity	NPC9161
0.8378	Intermediate Similarity	NPC49422
0.8378	Intermediate Similarity	NPC45296
0.8375	Intermediate Similarity	NPC20853
0.8375	Intermediate Similarity	NPC87489
0.8375	Intermediate Similarity	NPC296701
0.8375	Intermediate Similarity	NPC202389
0.8375	Intermediate Similarity	NPC218616
0.8375	Intermediate Similarity	NPC151519
0.8333	Intermediate Similarity	NPC470396
0.8333	Intermediate Similarity	NPC83351
0.8333	Intermediate Similarity	NPC22955
0.8333	Intermediate Similarity	NPC476314
0.8333	Intermediate Similarity	NPC476039

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 NPC34019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1734
0.2-0.3	4602
0.3-0.4	1882
0.4-0.5	360
0.5-0.6	156
0.6-0.7	168
0.7-0.8	46
0.8-0.85	17
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9718	High Similarity	NPD6942	Approved
0.9718	High Similarity	NPD7339	Approved
0.9054	High Similarity	NPD3701	Clinical (unspecified phase)
0.8625	High Similarity	NPD4786	Approved
0.859	High Similarity	NPD7525	Registered
0.8533	High Similarity	NPD4785	Approved
0.8533	High Similarity	NPD4784	Approved
0.8533	High Similarity	NPD6924	Approved
0.8533	High Similarity	NPD6926	Approved
0.8514	High Similarity	NPD7151	Approved
0.8514	High Similarity	NPD4243	Approved
0.8514	High Similarity	NPD7150	Approved
0.8514	High Similarity	NPD7152	Approved
0.8493	Intermediate Similarity	NPD6922	Approved
0.8493	Intermediate Similarity	NPD6923	Approved
0.8378	Intermediate Similarity	NPD7144	Approved
0.8378	Intermediate Similarity	NPD7143	Approved
0.8375	Intermediate Similarity	NPD3667	Approved
0.8312	Intermediate Similarity	NPD6933	Approved
0.8095	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7645	Phase 2
0.8	Intermediate Similarity	NPD6929	Approved
0.7949	Intermediate Similarity	NPD4190	Phase 3
0.7949	Intermediate Similarity	NPD5275	Approved
0.7907	Intermediate Similarity	NPD5328	Approved
0.7901	Intermediate Similarity	NPD6930	Phase 2
0.7901	Intermediate Similarity	NPD6931	Approved
0.7901	Intermediate Similarity	NPD4748	Discontinued
0.7805	Intermediate Similarity	NPD6902	Approved
0.7765	Intermediate Similarity	NPD3618	Phase 1
0.775	Intermediate Similarity	NPD6932	Approved
0.775	Intermediate Similarity	NPD5776	Phase 2
0.775	Intermediate Similarity	NPD6925	Approved
0.7738	Intermediate Similarity	NPD3666	Approved
0.7738	Intermediate Similarity	NPD3665	Phase 1
0.7738	Intermediate Similarity	NPD3133	Approved
0.7727	Intermediate Similarity	NPD6079	Approved
0.7683	Intermediate Similarity	NPD7509	Discontinued
0.7654	Intermediate Similarity	NPD7145	Approved
0.764	Intermediate Similarity	NPD6399	Phase 3
0.7619	Intermediate Similarity	NPD6695	Phase 3
0.7561	Intermediate Similarity	NPD4195	Approved
0.7561	Intermediate Similarity	NPD6683	Phase 2
0.7529	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3668	Phase 3
0.747	Intermediate Similarity	NPD7514	Phase 3
0.7444	Intermediate Similarity	NPD4202	Approved
0.7442	Intermediate Similarity	NPD6893	Approved
0.7439	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5279	Phase 3
0.7303	Intermediate Similarity	NPD4753	Phase 2
0.7294	Intermediate Similarity	NPD4221	Approved
0.7294	Intermediate Similarity	NPD4223	Phase 3
0.7284	Intermediate Similarity	NPD8264	Approved
0.7273	Intermediate Similarity	NPD7524	Approved
0.7273	Intermediate Similarity	NPD7750	Discontinued
0.7262	Intermediate Similarity	NPD7332	Phase 2
0.7241	Intermediate Similarity	NPD5329	Approved
0.7241	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5221	Approved
0.7204	Intermediate Similarity	NPD5222	Approved
0.7204	Intermediate Similarity	NPD4697	Phase 3
0.7176	Intermediate Similarity	NPD6898	Phase 1
0.7128	Intermediate Similarity	NPD4755	Approved
0.7128	Intermediate Similarity	NPD5173	Approved
0.7126	Intermediate Similarity	NPD4197	Approved
0.7011	Intermediate Similarity	NPD4788	Approved
0.6979	Remote Similarity	NPD4700	Approved
0.6979	Remote Similarity	NPD5286	Approved
0.6979	Remote Similarity	NPD4696	Approved
0.6979	Remote Similarity	NPD5285	Approved
0.6966	Remote Similarity	NPD7146	Approved
0.6966	Remote Similarity	NPD7334	Approved
0.6966	Remote Similarity	NPD6684	Approved
0.6966	Remote Similarity	NPD5205	Approved
0.6966	Remote Similarity	NPD4138	Approved
0.6966	Remote Similarity	NPD4693	Phase 3
0.6966	Remote Similarity	NPD4688	Approved
0.6966	Remote Similarity	NPD5330	Approved
0.6966	Remote Similarity	NPD7521	Approved
0.6966	Remote Similarity	NPD4689	Approved
0.6966	Remote Similarity	NPD6409	Approved
0.6966	Remote Similarity	NPD4690	Approved
0.6957	Remote Similarity	NPD7087	Discontinued
0.6957	Remote Similarity	NPD7515	Phase 2
0.6947	Remote Similarity	NPD6084	Phase 2
0.6947	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD6051	Approved
0.6915	Remote Similarity	NPD4629	Approved
0.6915	Remote Similarity	NPD5210	Approved
0.6907	Remote Similarity	NPD5223	Approved
0.6875	Remote Similarity	NPD7638	Approved
0.6875	Remote Similarity	NPD5290	Discontinued
0.6875	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5224	Approved
0.6837	Remote Similarity	NPD5225	Approved
0.6837	Remote Similarity	NPD5226	Approved
0.6837	Remote Similarity	NPD4633	Approved
0.6837	Remote Similarity	NPD5211	Phase 2
0.6824	Remote Similarity	NPD3617	Approved
0.6813	Remote Similarity	NPD6903	Approved
0.6813	Remote Similarity	NPD5737	Approved
0.6813	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6672	Approved
0.6813	Remote Similarity	NPD4723	Approved
0.6813	Remote Similarity	NPD4722	Approved
0.6804	Remote Similarity	NPD7640	Approved
0.6804	Remote Similarity	NPD7639	Approved
0.68	Remote Similarity	NPD6675	Approved
0.68	Remote Similarity	NPD5739	Approved
0.68	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD6402	Approved
0.679	Remote Similarity	NPD4787	Phase 1
0.6778	Remote Similarity	NPD5280	Approved
0.6778	Remote Similarity	NPD4694	Approved
0.6778	Remote Similarity	NPD5690	Phase 2
0.6768	Remote Similarity	NPD5174	Approved
0.6768	Remote Similarity	NPD4754	Approved
0.6768	Remote Similarity	NPD5175	Approved
0.6707	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6634	Remote Similarity	NPD4768	Approved
0.6634	Remote Similarity	NPD4767	Approved
0.6632	Remote Similarity	NPD7748	Approved
0.6602	Remote Similarity	NPD6372	Approved
0.6602	Remote Similarity	NPD6373	Approved
0.6596	Remote Similarity	NPD8034	Phase 2
0.6596	Remote Similarity	NPD8035	Phase 2
0.6596	Remote Similarity	NPD7637	Suspended
0.6593	Remote Similarity	NPD6098	Approved
0.6593	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4692	Approved
0.6591	Remote Similarity	NPD4139	Approved
0.6585	Remote Similarity	NPD4747	Approved
0.6569	Remote Similarity	NPD5701	Approved
0.6569	Remote Similarity	NPD5697	Approved
0.6566	Remote Similarity	NPD4159	Approved
0.6562	Remote Similarity	NPD5695	Phase 3
0.6562	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7102	Approved
0.6538	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD7290	Approved
0.6531	Remote Similarity	NPD5696	Approved
0.6526	Remote Similarity	NPD5133	Approved
0.6505	Remote Similarity	NPD4729	Approved
0.6505	Remote Similarity	NPD4730	Approved
0.6505	Remote Similarity	NPD5128	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD5168	Approved
0.6489	Remote Similarity	NPD7136	Phase 2
0.6486	Remote Similarity	NPD342	Phase 1
0.6481	Remote Similarity	NPD7115	Discovery
0.6476	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6650	Approved
0.6476	Remote Similarity	NPD6847	Approved
0.6476	Remote Similarity	NPD6649	Approved
0.6476	Remote Similarity	NPD6869	Approved
0.6476	Remote Similarity	NPD6617	Approved
0.6476	Remote Similarity	NPD8130	Phase 1
0.6463	Remote Similarity	NPD4137	Phase 3
0.6463	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD7902	Approved
0.6421	Remote Similarity	NPD5284	Approved
0.6421	Remote Similarity	NPD5281	Approved
0.6415	Remote Similarity	NPD6882	Approved
0.6415	Remote Similarity	NPD8297	Approved
0.6413	Remote Similarity	NPD4519	Discontinued
0.6413	Remote Similarity	NPD4623	Approved
0.641	Remote Similarity	NPD368	Approved
0.6408	Remote Similarity	NPD6412	Phase 2
0.6395	Remote Similarity	NPD6117	Approved
0.6386	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4691	Approved
0.6386	Remote Similarity	NPD4245	Approved
0.6386	Remote Similarity	NPD6939	Phase 2
0.6386	Remote Similarity	NPD4789	Approved
0.6386	Remote Similarity	NPD4244	Approved
0.6383	Remote Similarity	NPD6673	Approved
0.6383	Remote Similarity	NPD6904	Approved
0.6383	Remote Similarity	NPD6080	Approved
0.6381	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4634	Approved
0.6381	Remote Similarity	NPD5135	Approved
0.6381	Remote Similarity	NPD5247	Approved
0.6381	Remote Similarity	NPD5249	Phase 3
0.6381	Remote Similarity	NPD5248	Approved
0.6381	Remote Similarity	NPD5251	Approved
0.6381	Remote Similarity	NPD5250	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