NPASS Compound

Structure

NPC121984 OpenBabel07101718332D 22 24 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 -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 2 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 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 14 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 15 6 1 6 0 0 0 15 18 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 18 20 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	3.754
LogD:	3.107
LogS:	-3.603
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.784
Synthetic Accessibility Score:	4.582
Fsp3:	0.75
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:	-4.678
MDCK Permeability:	1.2226877515786327e-05
Pgp-inhibitor:	0.511
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.381
Plasma Protein Binding (PPB):	55.93052673339844%
Volume Distribution (VD):	1.792
Pgp-substrate:	36.22578430175781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.41
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.703
CYP2C9-inhibitor:	0.5
CYP2C9-substrate:	0.193
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.372
CYP3A4-inhibitor:	0.341
CYP3A4-substrate:	0.318

ADMET: Excretion

Clearance (CL):	14.181
Half-life (T1/2):	0.439

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.917
Maximum Recommended Daily Dose:	0.734
Skin Sensitization:	0.94
Carcinogencity:	0.772
Eye Corrosion:	0.923
Eye Irritation:	0.591
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC121984

Natural Product ID:	NPC121984
*Common Name:**	16-Hydroxy-11-Oxocass-12,14-Diene
IUPAC Name:	(4aS,4bS,8aS,10aR)-2-(2-hydroxyethyl)-4b,8,8-trimethyl-1-methylidene-4a,5,6,7,8a,9,10,10a-octahydrophenanthren-4-one
Synonyms:
Standard InCHIKey:	SPVICFWCEKFWAW-BOLBYERCSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13-14(8-11-21)12-16(22)18-15(13)6-7-17-19(2,3)9-5-10-20(17,18)4/h12,15,17-18,21H,1,5-11H2,2-4H3/t15-,17-,18+,20-/m0/s1
SMILES:	OCCC1=CC(=O)[C@H]2[C@H](C1=C)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2381686
PubChem CID:	71615305
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
NPO33322	caesalpinia volkensii	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[23562058]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	22790.0	nM	PMID[552606]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	17260.0	nM	PMID[552606]

☑ 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 NPC121984 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	173
0.1-0.2	988
0.2-0.3	4341
0.3-0.4	12725
0.4-0.5	11213
0.5-0.6	6941
0.6-0.7	4179
0.7-0.8	1856
0.8-0.85	225
0.85-0.9	52
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC2482
0.9221	High Similarity	NPC474113
0.9012	High Similarity	NPC469948
0.8902	High Similarity	NPC474733
0.8902	High Similarity	NPC474732
0.8902	High Similarity	NPC94666
0.8902	High Similarity	NPC31564
0.8902	High Similarity	NPC145879
0.8902	High Similarity	NPC474778
0.8889	High Similarity	NPC237712
0.8889	High Similarity	NPC329043
0.8889	High Similarity	NPC321187
0.8889	High Similarity	NPC214043
0.8889	High Similarity	NPC85774
0.8889	High Similarity	NPC161423
0.8889	High Similarity	NPC227064
0.8889	High Similarity	NPC58841
0.8875	High Similarity	NPC310989
0.8875	High Similarity	NPC151519
0.8861	High Similarity	NPC472478
0.8846	High Similarity	NPC189485
0.8831	High Similarity	NPC263582
0.8831	High Similarity	NPC470525
0.8795	High Similarity	NPC475740
0.8795	High Similarity	NPC58063
0.8795	High Similarity	NPC136548
0.875	High Similarity	NPC116797
0.875	High Similarity	NPC14151
0.875	High Similarity	NPC3915
0.875	High Similarity	NPC225515
0.8718	High Similarity	NPC165711
0.8718	High Similarity	NPC197659
0.8675	High Similarity	NPC473168
0.8675	High Similarity	NPC327115
0.8659	High Similarity	NPC473246
0.8659	High Similarity	NPC221758
0.8659	High Similarity	NPC476412
0.8659	High Similarity	NPC59453
0.8659	High Similarity	NPC180834
0.8642	High Similarity	NPC103486
0.8642	High Similarity	NPC212083
0.8625	High Similarity	NPC476809
0.8625	High Similarity	NPC108955
0.8608	High Similarity	NPC62336
0.8588	High Similarity	NPC119416
0.8588	High Similarity	NPC268406
0.8588	High Similarity	NPC1015
0.8588	High Similarity	NPC186688
0.8588	High Similarity	NPC31985
0.8588	High Similarity	NPC477973
0.8588	High Similarity	NPC26959
0.8571	High Similarity	NPC93778
0.8571	High Similarity	NPC141292
0.8554	High Similarity	NPC476426
0.8554	High Similarity	NPC6185
0.8554	High Similarity	NPC241512
0.8554	High Similarity	NPC470574
0.8537	High Similarity	NPC307258
0.8537	High Similarity	NPC102197
0.8519	High Similarity	NPC471898
0.8519	High Similarity	NPC55869
0.8519	High Similarity	NPC6663
0.8519	High Similarity	NPC278459
0.8506	High Similarity	NPC250575
0.8506	High Similarity	NPC211230
0.8506	High Similarity	NPC134826
0.85	High Similarity	NPC308038
0.85	High Similarity	NPC27817
0.85	High Similarity	NPC472490
0.85	High Similarity	NPC476177
0.8488	Intermediate Similarity	NPC48010
0.8488	Intermediate Similarity	NPC129913
0.8481	Intermediate Similarity	NPC472300
0.8471	Intermediate Similarity	NPC472802
0.8471	Intermediate Similarity	NPC328539
0.8471	Intermediate Similarity	NPC292491
0.8471	Intermediate Similarity	NPC206060
0.8471	Intermediate Similarity	NPC310752
0.8471	Intermediate Similarity	NPC471722
0.8462	Intermediate Similarity	NPC114236
0.8452	Intermediate Similarity	NPC475022
0.8452	Intermediate Similarity	NPC51014
0.8452	Intermediate Similarity	NPC158393
0.8452	Intermediate Similarity	NPC118648
0.8452	Intermediate Similarity	NPC20688
0.8452	Intermediate Similarity	NPC472974
0.8452	Intermediate Similarity	NPC222613
0.8452	Intermediate Similarity	NPC472986
0.8452	Intermediate Similarity	NPC472985
0.8452	Intermediate Similarity	NPC470955
0.8434	Intermediate Similarity	NPC472265
0.8434	Intermediate Similarity	NPC53385
0.8434	Intermediate Similarity	NPC82902
0.8415	Intermediate Similarity	NPC48362
0.8415	Intermediate Similarity	NPC193347
0.8409	Intermediate Similarity	NPC474328
0.8409	Intermediate Similarity	NPC473162
0.8409	Intermediate Similarity	NPC473172
0.8409	Intermediate Similarity	NPC474882
0.8395	Intermediate Similarity	NPC172013
0.8391	Intermediate Similarity	NPC19114
0.8391	Intermediate Similarity	NPC131872
0.8375	Intermediate Similarity	NPC178852
0.8375	Intermediate Similarity	NPC471409
0.8375	Intermediate Similarity	NPC275494
0.8375	Intermediate Similarity	NPC475994
0.8372	Intermediate Similarity	NPC184663
0.8372	Intermediate Similarity	NPC310010
0.8372	Intermediate Similarity	NPC473999
0.8372	Intermediate Similarity	NPC477943
0.8372	Intermediate Similarity	NPC326627
0.8372	Intermediate Similarity	NPC309603
0.8354	Intermediate Similarity	NPC69143
0.8354	Intermediate Similarity	NPC309399
0.8354	Intermediate Similarity	NPC92080
0.8354	Intermediate Similarity	NPC250621
0.8354	Intermediate Similarity	NPC180886
0.8353	Intermediate Similarity	NPC73064
0.8353	Intermediate Similarity	NPC470523
0.8333	Intermediate Similarity	NPC132228
0.8333	Intermediate Similarity	NPC474218
0.8333	Intermediate Similarity	NPC470299
0.8333	Intermediate Similarity	NPC474680
0.8333	Intermediate Similarity	NPC8518
0.8333	Intermediate Similarity	NPC471224
0.8333	Intermediate Similarity	NPC263997
0.8333	Intermediate Similarity	NPC32037
0.8333	Intermediate Similarity	NPC274724
0.8333	Intermediate Similarity	NPC133954
0.8315	Intermediate Similarity	NPC280725
0.8313	Intermediate Similarity	NPC291999
0.8313	Intermediate Similarity	NPC53733
0.8313	Intermediate Similarity	NPC309309
0.8313	Intermediate Similarity	NPC70834
0.8313	Intermediate Similarity	NPC105803
0.8313	Intermediate Similarity	NPC64600
0.8295	Intermediate Similarity	NPC263780
0.8295	Intermediate Similarity	NPC109305
0.8295	Intermediate Similarity	NPC474736
0.8293	Intermediate Similarity	NPC473420
0.8293	Intermediate Similarity	NPC90055
0.8293	Intermediate Similarity	NPC142244
0.8293	Intermediate Similarity	NPC470298
0.8293	Intermediate Similarity	NPC473217
0.8293	Intermediate Similarity	NPC136150
0.8276	Intermediate Similarity	NPC85173
0.8276	Intermediate Similarity	NPC69622
0.8272	Intermediate Similarity	NPC281138
0.8256	Intermediate Similarity	NPC474677
0.8256	Intermediate Similarity	NPC1753
0.8256	Intermediate Similarity	NPC328313
0.8256	Intermediate Similarity	NPC474511
0.8256	Intermediate Similarity	NPC470524
0.8256	Intermediate Similarity	NPC158778
0.825	Intermediate Similarity	NPC325946
0.825	Intermediate Similarity	NPC266193
0.825	Intermediate Similarity	NPC106078
0.825	Intermediate Similarity	NPC74995
0.825	Intermediate Similarity	NPC257666
0.8235	Intermediate Similarity	NPC213412
0.8235	Intermediate Similarity	NPC155011
0.8235	Intermediate Similarity	NPC72133
0.8235	Intermediate Similarity	NPC89077
0.8235	Intermediate Similarity	NPC475862
0.8235	Intermediate Similarity	NPC82979
0.8235	Intermediate Similarity	NPC74363
0.8235	Intermediate Similarity	NPC194417
0.8235	Intermediate Similarity	NPC469994
0.8228	Intermediate Similarity	NPC192540
0.8228	Intermediate Similarity	NPC279666
0.8222	Intermediate Similarity	NPC473164
0.8214	Intermediate Similarity	NPC33913
0.8214	Intermediate Similarity	NPC144258
0.8214	Intermediate Similarity	NPC96095
0.8202	Intermediate Similarity	NPC474690
0.8202	Intermediate Similarity	NPC23170
0.8202	Intermediate Similarity	NPC196485
0.8202	Intermediate Similarity	NPC245972
0.8193	Intermediate Similarity	NPC251779
0.8193	Intermediate Similarity	NPC69101
0.8193	Intermediate Similarity	NPC320514
0.8193	Intermediate Similarity	NPC93590
0.8193	Intermediate Similarity	NPC302661
0.8193	Intermediate Similarity	NPC238991
0.8193	Intermediate Similarity	NPC73882
0.8182	Intermediate Similarity	NPC145067
0.8182	Intermediate Similarity	NPC470036
0.8182	Intermediate Similarity	NPC4036
0.8182	Intermediate Similarity	NPC272746
0.8182	Intermediate Similarity	NPC174167
0.8182	Intermediate Similarity	NPC473998
0.8182	Intermediate Similarity	NPC233455
0.8182	Intermediate Similarity	NPC158030
0.8182	Intermediate Similarity	NPC475806
0.8182	Intermediate Similarity	NPC168027
0.8182	Intermediate Similarity	NPC301244
0.8182	Intermediate Similarity	NPC65120
0.8182	Intermediate Similarity	NPC185936
0.8171	Intermediate Similarity	NPC469637
0.8161	Intermediate Similarity	NPC68148

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 NPC121984 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1263
0.2-0.3	3634
0.3-0.4	2724
0.4-0.5	856
0.5-0.6	217
0.6-0.7	179
0.7-0.8	99
0.8-0.85	12
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD3666	Approved
0.8889	High Similarity	NPD3133	Approved
0.8889	High Similarity	NPD3665	Phase 1
0.8875	High Similarity	NPD3667	Approved
0.8675	High Similarity	NPD3618	Phase 1
0.8675	High Similarity	NPD5279	Phase 3
0.8659	High Similarity	NPD4786	Approved
0.8625	High Similarity	NPD4695	Discontinued
0.8415	Intermediate Similarity	NPD4221	Approved
0.8415	Intermediate Similarity	NPD4223	Phase 3
0.8372	Intermediate Similarity	NPD4753	Phase 2
0.8372	Intermediate Similarity	NPD5328	Approved
0.8235	Intermediate Similarity	NPD4694	Approved
0.8235	Intermediate Similarity	NPD5280	Approved
0.8214	Intermediate Similarity	NPD4197	Approved
0.8182	Intermediate Similarity	NPD6079	Approved
0.8182	Intermediate Similarity	NPD7515	Phase 2
0.8161	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD3617	Approved
0.8118	Intermediate Similarity	NPD5329	Approved
0.809	Intermediate Similarity	NPD4202	Approved
0.8023	Intermediate Similarity	NPD4623	Approved
0.8023	Intermediate Similarity	NPD4693	Phase 3
0.8023	Intermediate Similarity	NPD4519	Discontinued
0.8023	Intermediate Similarity	NPD4688	Approved
0.8023	Intermediate Similarity	NPD5205	Approved
0.8023	Intermediate Similarity	NPD4690	Approved
0.8023	Intermediate Similarity	NPD4689	Approved
0.8023	Intermediate Similarity	NPD4138	Approved
0.8	Intermediate Similarity	NPD3668	Phase 3
0.7912	Intermediate Similarity	NPD5210	Approved
0.7912	Intermediate Similarity	NPD4629	Approved
0.7875	Intermediate Similarity	NPD4058	Approved
0.7826	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4697	Phase 3
0.7826	Intermediate Similarity	NPD5221	Approved
0.7826	Intermediate Similarity	NPD5222	Approved
0.7821	Intermediate Similarity	NPD4137	Phase 3
0.7816	Intermediate Similarity	NPD6409	Approved
0.7816	Intermediate Similarity	NPD7146	Approved
0.7816	Intermediate Similarity	NPD5330	Approved
0.7816	Intermediate Similarity	NPD6684	Approved
0.7816	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7334	Approved
0.7816	Intermediate Similarity	NPD5690	Phase 2
0.7816	Intermediate Similarity	NPD7521	Approved
0.7802	Intermediate Similarity	NPD7748	Approved
0.7778	Intermediate Similarity	NPD5281	Approved
0.7778	Intermediate Similarity	NPD5284	Approved
0.7742	Intermediate Similarity	NPD6084	Phase 2
0.7742	Intermediate Similarity	NPD6083	Phase 2
0.7742	Intermediate Similarity	NPD5173	Approved
0.7742	Intermediate Similarity	NPD4755	Approved
0.7722	Intermediate Similarity	NPD4691	Approved
0.7722	Intermediate Similarity	NPD4747	Approved
0.7692	Intermediate Similarity	NPD6399	Phase 3
0.7683	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4788	Approved
0.7667	Intermediate Similarity	NPD4096	Approved
0.7654	Intermediate Similarity	NPD5733	Approved
0.7654	Intermediate Similarity	NPD4687	Approved
0.764	Intermediate Similarity	NPD6903	Approved
0.764	Intermediate Similarity	NPD5737	Approved
0.764	Intermediate Similarity	NPD6672	Approved
0.764	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4518	Approved
0.7625	Intermediate Similarity	NPD5276	Approved
0.7619	Intermediate Similarity	NPD4195	Approved
0.7579	Intermediate Similarity	NPD5285	Approved
0.7579	Intermediate Similarity	NPD5286	Approved
0.7579	Intermediate Similarity	NPD4700	Approved
0.7579	Intermediate Similarity	NPD4696	Approved
0.7561	Intermediate Similarity	NPD7339	Approved
0.7561	Intermediate Similarity	NPD6942	Approved
0.7553	Intermediate Similarity	NPD7902	Approved
0.7529	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD5133	Approved
0.7474	Intermediate Similarity	NPD5696	Approved
0.7439	Intermediate Similarity	NPD6924	Approved
0.7439	Intermediate Similarity	NPD6926	Approved
0.7423	Intermediate Similarity	NPD4633	Approved
0.7423	Intermediate Similarity	NPD5225	Approved
0.7423	Intermediate Similarity	NPD5224	Approved
0.7423	Intermediate Similarity	NPD5226	Approved
0.7423	Intermediate Similarity	NPD5211	Phase 2
0.7391	Intermediate Similarity	NPD6411	Approved
0.7347	Intermediate Similarity	NPD4754	Approved
0.7347	Intermediate Similarity	NPD5175	Approved
0.7347	Intermediate Similarity	NPD5174	Approved
0.7333	Intermediate Similarity	NPD3573	Approved
0.7303	Intermediate Similarity	NPD1696	Phase 3
0.7283	Intermediate Similarity	NPD5207	Approved
0.7283	Intermediate Similarity	NPD5692	Phase 3
0.7273	Intermediate Similarity	NPD5141	Approved
0.7262	Intermediate Similarity	NPD6933	Approved
0.7253	Intermediate Similarity	NPD5208	Approved
0.725	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4692	Approved
0.7241	Intermediate Similarity	NPD4139	Approved
0.7234	Intermediate Similarity	NPD7900	Approved
0.7234	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7331	Phase 2
0.7209	Intermediate Similarity	NPD7645	Phase 2
0.7204	Intermediate Similarity	NPD5694	Approved
0.7204	Intermediate Similarity	NPD6050	Approved
0.72	Intermediate Similarity	NPD5739	Approved
0.72	Intermediate Similarity	NPD7128	Approved
0.72	Intermediate Similarity	NPD6675	Approved
0.72	Intermediate Similarity	NPD4767	Approved
0.72	Intermediate Similarity	NPD6402	Approved
0.72	Intermediate Similarity	NPD4768	Approved
0.7174	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6101	Approved
0.7174	Intermediate Similarity	NPD6904	Approved
0.7174	Intermediate Similarity	NPD6673	Approved
0.7174	Intermediate Similarity	NPD6080	Approved
0.716	Intermediate Similarity	NPD6922	Approved
0.716	Intermediate Similarity	NPD6923	Approved
0.7159	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6412	Phase 2
0.7129	Intermediate Similarity	NPD5701	Approved
0.7129	Intermediate Similarity	NPD5697	Approved
0.7111	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7341	Phase 2
0.7083	Intermediate Similarity	NPD7614	Phase 1
0.7073	Intermediate Similarity	NPD7143	Approved
0.7073	Intermediate Similarity	NPD7144	Approved
0.7059	Intermediate Similarity	NPD4729	Approved
0.7059	Intermediate Similarity	NPD6899	Approved
0.7059	Intermediate Similarity	NPD6881	Approved
0.7059	Intermediate Similarity	NPD4730	Approved
0.7059	Intermediate Similarity	NPD5128	Approved
0.7059	Intermediate Similarity	NPD7320	Approved
0.7059	Intermediate Similarity	NPD6011	Approved
0.7059	Intermediate Similarity	NPD5168	Approved
0.7033	Intermediate Similarity	NPD6098	Approved
0.7024	Intermediate Similarity	NPD4785	Approved
0.7024	Intermediate Similarity	NPD4784	Approved
0.7021	Intermediate Similarity	NPD5693	Phase 1
0.7011	Intermediate Similarity	NPD6929	Approved
0.699	Remote Similarity	NPD6372	Approved
0.699	Remote Similarity	NPD6012	Approved
0.699	Remote Similarity	NPD6373	Approved
0.699	Remote Similarity	NPD6014	Approved
0.699	Remote Similarity	NPD6013	Approved
0.6988	Remote Similarity	NPD7151	Approved
0.6988	Remote Similarity	NPD4243	Approved
0.6988	Remote Similarity	NPD7150	Approved
0.6988	Remote Similarity	NPD7152	Approved
0.6979	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3698	Phase 2
0.6941	Remote Similarity	NPD8264	Approved
0.6939	Remote Similarity	NPD7638	Approved
0.6932	Remote Similarity	NPD7525	Registered
0.6932	Remote Similarity	NPD7509	Discontinued
0.6932	Remote Similarity	NPD6930	Phase 2
0.6932	Remote Similarity	NPD6931	Approved
0.6923	Remote Similarity	NPD4634	Approved
0.6923	Remote Similarity	NPD5248	Approved
0.6923	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD5247	Approved
0.6923	Remote Similarity	NPD5135	Approved
0.6923	Remote Similarity	NPD5249	Phase 3
0.6923	Remote Similarity	NPD7290	Approved
0.6923	Remote Similarity	NPD5169	Approved
0.6923	Remote Similarity	NPD5250	Approved
0.6923	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5251	Approved
0.69	Remote Similarity	NPD5091	Approved
0.6889	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6001	Approved
0.6869	Remote Similarity	NPD6404	Discontinued
0.6869	Remote Similarity	NPD7640	Approved
0.6869	Remote Similarity	NPD7639	Approved
0.6867	Remote Similarity	NPD4245	Approved
0.6867	Remote Similarity	NPD4244	Approved
0.6867	Remote Similarity	NPD4789	Approved
0.6857	Remote Similarity	NPD5127	Approved
0.6857	Remote Similarity	NPD5215	Approved
0.6857	Remote Similarity	NPD8130	Phase 1
0.6857	Remote Similarity	NPD5217	Approved
0.6857	Remote Similarity	NPD6650	Approved
0.6857	Remote Similarity	NPD6617	Approved
0.6857	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6869	Approved
0.6857	Remote Similarity	NPD6649	Approved
0.6857	Remote Similarity	NPD6847	Approved
0.6857	Remote Similarity	NPD5216	Approved
0.6804	Remote Similarity	NPD5654	Approved
0.6792	Remote Similarity	NPD6882	Approved
0.6792	Remote Similarity	NPD8297	Approved
0.6786	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6932	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