NPASS Compound

Structure

NPC472932 OpenBabel07101718312D 35 38 0 0 1 0 0 0 0 0999 V2000 -0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 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 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 4.1622 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 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 -1.5180 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1871 5.1132 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 -0.9511 1.3090 0.0000 C 0 0 2 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 2.5981 -1.5000 0.0000 C 0 0 1 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 -0.9511 -0.3090 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8270 6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4743 6.2722 0.0000 O 0 0 0 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 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 5 29 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 21 1 0 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 16 31 1 0 0 0 0 17 19 1 0 0 0 0 17 32 1 0 0 0 0 18 1 1 1 0 0 0 18 21 1 0 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 21 29 1 6 0 0 0 22 26 1 0 0 0 0 22 33 2 0 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 34 2 0 0 0 0 25 30 1 6 0 0 0 25 35 1 0 0 0 0 26 28 1 0 0 0 0 28 4 1 6 0 0 0 29 30 1 6 0 0 0 30 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	526.615
LogP:	3.433
LogD:	3.507
LogS:	-4.305
# Rotatable Bonds:	6
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	5.069
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.033
MDCK Permeability:	1.0115996701642871e-05
Pgp-inhibitor:	0.737
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.639

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	85.05610656738281%
Volume Distribution (VD):	0.67
Pgp-substrate:	4.746127605438232%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.235
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.26
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.736
CYP3A4-substrate:	0.638

ADMET: Excretion

Clearance (CL):	4.477
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.314
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.429
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.611
Carcinogencity:	0.177
Eye Corrosion:	0.004
Eye Irritation:	0.055
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC472932

Natural Product ID:	NPC472932
*Common Name:**	NCWPXHMUBMRCHV-KEMHIYJBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NCWPXHMUBMRCHV-KEMHIYJBSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-18(8-7-9-19(16-31)17-32)21-14-25(35)30(6)20-10-11-23-27(2,3)24(34)12-13-28(23,4)26(20)22(33)15-29(21,30)5/h9,18,21,23,25,31-32,35H,7-8,10-17H2,1-6H3/t18-,21-,23+,25-,28+,29-,30-/m1/s1
SMILES:	CC(CCC=C(CO)CO)C1CC(C2(C1(CC(=O)C3=C2CCC4C3(CCC(=O)C4(C)C)C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594150
PubChem CID:	n.a.
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
NPO33020	ganoderma leucocontextum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Tibetan	n.a.	PMID[26287401]

☑ 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	4

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1088	Individual Protein	3-hydroxy-3-methylglutaryl-coenzyme A reductase	Sus scrofa	IC50	>	100000.0	nM	PMID[520500]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	200000.0	nM	PMID[520500]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	200000.0	nM	PMID[520500]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[520500]

☑ 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 NPC472932 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	162
0.1-0.2	1064
0.2-0.3	4573
0.3-0.4	11591
0.4-0.5	11153
0.5-0.6	6842
0.6-0.7	5341
0.7-0.8	1612
0.8-0.85	246
0.85-0.9	88
0.9-0.95	23
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9551	High Similarity	NPC472930
0.9457	High Similarity	NPC197386
0.9333	High Similarity	NPC472942
0.9263	High Similarity	NPC111323
0.9158	High Similarity	NPC473424
0.9158	High Similarity	NPC195290
0.9158	High Similarity	NPC204450
0.9158	High Similarity	NPC87351
0.913	High Similarity	NPC469995
0.913	High Similarity	NPC173875
0.913	High Similarity	NPC174948
0.913	High Similarity	NPC318282
0.9121	High Similarity	NPC69454
0.9111	High Similarity	NPC69622
0.9062	High Similarity	NPC311612
0.9062	High Similarity	NPC236390
0.9043	High Similarity	NPC235464
0.9043	High Similarity	NPC166745
0.9032	High Similarity	NPC249954
0.9032	High Similarity	NPC328371
0.9011	High Similarity	NPC63748
0.9	High Similarity	NPC477943
0.9	High Similarity	NPC123912
0.8977	High Similarity	NPC474083
0.8936	High Similarity	NPC18319
0.8925	High Similarity	NPC259286
0.8901	High Similarity	NPC48010
0.8876	High Similarity	NPC469994
0.8864	High Similarity	NPC473246
0.8842	High Similarity	NPC471717
0.8842	High Similarity	NPC10364
0.8804	High Similarity	NPC473998
0.8791	High Similarity	NPC473999
0.8791	High Similarity	NPC2983
0.8791	High Similarity	NPC31985
0.8791	High Similarity	NPC309603
0.8791	High Similarity	NPC1015
0.8791	High Similarity	NPC86319
0.8791	High Similarity	NPC275740
0.8788	High Similarity	NPC185
0.8778	High Similarity	NPC317590
0.8764	High Similarity	NPC471224
0.8764	High Similarity	NPC469948
0.8763	High Similarity	NPC477915
0.875	High Similarity	NPC474720
0.875	High Similarity	NPC51370
0.875	High Similarity	NPC287833
0.875	High Similarity	NPC205899
0.871	High Similarity	NPC206810
0.871	High Similarity	NPC25750
0.871	High Similarity	NPC250575
0.871	High Similarity	NPC474736
0.87	High Similarity	NPC65941
0.8696	High Similarity	NPC320026
0.8687	High Similarity	NPC149047
0.8687	High Similarity	NPC60681
0.8681	High Similarity	NPC131470
0.8681	High Similarity	NPC143767
0.8681	High Similarity	NPC471722
0.8673	High Similarity	NPC26478
0.8667	High Similarity	NPC31564
0.8667	High Similarity	NPC474733
0.8667	High Similarity	NPC222613
0.8667	High Similarity	NPC474778
0.8667	High Similarity	NPC145879
0.8667	High Similarity	NPC475022
0.8667	High Similarity	NPC474732
0.8667	High Similarity	NPC118648
0.866	High Similarity	NPC302537
0.866	High Similarity	NPC99411
0.866	High Similarity	NPC163372
0.866	High Similarity	NPC472924
0.8652	High Similarity	NPC321187
0.8652	High Similarity	NPC85774
0.8652	High Similarity	NPC161423
0.8652	High Similarity	NPC227064
0.8652	High Similarity	NPC82902
0.8652	High Similarity	NPC329043
0.8652	High Similarity	NPC214043
0.8652	High Similarity	NPC58841
0.8646	High Similarity	NPC147954
0.8632	High Similarity	NPC471463
0.8632	High Similarity	NPC472941
0.8632	High Similarity	NPC456
0.8617	High Similarity	NPC184870
0.8617	High Similarity	NPC8993
0.8617	High Similarity	NPC166906
0.8614	High Similarity	NPC214644
0.8602	High Similarity	NPC233116
0.8602	High Similarity	NPC475806
0.86	High Similarity	NPC220229
0.86	High Similarity	NPC83744
0.86	High Similarity	NPC477916
0.86	High Similarity	NPC475060
0.8587	High Similarity	NPC214387
0.8587	High Similarity	NPC310010
0.8587	High Similarity	NPC326627
0.8587	High Similarity	NPC186688
0.8586	High Similarity	NPC204833
0.8586	High Similarity	NPC209502
0.8571	High Similarity	NPC308726
0.8571	High Similarity	NPC58063
0.8571	High Similarity	NPC56498
0.8571	High Similarity	NPC119601
0.8571	High Similarity	NPC185530
0.8571	High Similarity	NPC475740
0.8557	High Similarity	NPC154072
0.8556	High Similarity	NPC472931
0.8556	High Similarity	NPC472940
0.8556	High Similarity	NPC474218
0.8542	High Similarity	NPC18509
0.8542	High Similarity	NPC320306
0.8539	High Similarity	NPC476082
0.8539	High Similarity	NPC278648
0.8526	High Similarity	NPC470016
0.8526	High Similarity	NPC37646
0.8526	High Similarity	NPC241156
0.8526	High Similarity	NPC317586
0.8515	High Similarity	NPC329417
0.8515	High Similarity	NPC177064
0.8515	High Similarity	NPC217201
0.8511	High Similarity	NPC243866
0.85	High Similarity	NPC296945
0.85	High Similarity	NPC85829
0.85	High Similarity	NPC202167
0.85	High Similarity	NPC260268
0.85	High Similarity	NPC49958
0.85	High Similarity	NPC302607
0.85	High Similarity	NPC152695
0.85	High Similarity	NPC476027
0.85	High Similarity	NPC214264
0.85	High Similarity	NPC48733
0.85	High Similarity	NPC319077
0.85	High Similarity	NPC257353
0.85	High Similarity	NPC97202
0.85	High Similarity	NPC50692
0.85	High Similarity	NPC171137
0.85	High Similarity	NPC150531
0.8495	Intermediate Similarity	NPC171441
0.8495	Intermediate Similarity	NPC183283
0.8495	Intermediate Similarity	NPC477149
0.8495	Intermediate Similarity	NPC477147
0.8485	Intermediate Similarity	NPC55872
0.8478	Intermediate Similarity	NPC328313
0.8478	Intermediate Similarity	NPC328539
0.8462	Intermediate Similarity	NPC327115
0.8462	Intermediate Similarity	NPC72133
0.8444	Intermediate Similarity	NPC59453
0.8444	Intermediate Similarity	NPC221758
0.8438	Intermediate Similarity	NPC328162
0.8438	Intermediate Similarity	NPC243525
0.8438	Intermediate Similarity	NPC3772
0.8438	Intermediate Similarity	NPC173272
0.8438	Intermediate Similarity	NPC96859
0.8438	Intermediate Similarity	NPC95565
0.8438	Intermediate Similarity	NPC305483
0.8438	Intermediate Similarity	NPC125622
0.8438	Intermediate Similarity	NPC155676
0.8438	Intermediate Similarity	NPC49371
0.8438	Intermediate Similarity	NPC117133
0.8438	Intermediate Similarity	NPC40765
0.8431	Intermediate Similarity	NPC11710
0.8421	Intermediate Similarity	NPC111015
0.8421	Intermediate Similarity	NPC474690
0.8421	Intermediate Similarity	NPC473162
0.8416	Intermediate Similarity	NPC472925
0.8404	Intermediate Similarity	NPC472978
0.8404	Intermediate Similarity	NPC185936
0.8404	Intermediate Similarity	NPC168027
0.8404	Intermediate Similarity	NPC107690
0.8404	Intermediate Similarity	NPC19114
0.84	Intermediate Similarity	NPC75531
0.84	Intermediate Similarity	NPC28656
0.84	Intermediate Similarity	NPC149124
0.8387	Intermediate Similarity	NPC26959
0.8387	Intermediate Similarity	NPC472970
0.8387	Intermediate Similarity	NPC268406
0.8387	Intermediate Similarity	NPC472971
0.8387	Intermediate Similarity	NPC54689
0.8387	Intermediate Similarity	NPC76879
0.837	Intermediate Similarity	NPC287079
0.837	Intermediate Similarity	NPC90652
0.837	Intermediate Similarity	NPC136548
0.8367	Intermediate Similarity	NPC327431
0.8367	Intermediate Similarity	NPC144956
0.8367	Intermediate Similarity	NPC476274
0.8367	Intermediate Similarity	NPC218383
0.8367	Intermediate Similarity	NPC83709
0.8365	Intermediate Similarity	NPC221144
0.8352	Intermediate Similarity	NPC474853
0.8352	Intermediate Similarity	NPC179006
0.8352	Intermediate Similarity	NPC202868
0.8351	Intermediate Similarity	NPC106557
0.8351	Intermediate Similarity	NPC121339
0.8351	Intermediate Similarity	NPC107243
0.8351	Intermediate Similarity	NPC475894
0.8351	Intermediate Similarity	NPC190554
0.8351	Intermediate Similarity	NPC43747
0.8333	Intermediate Similarity	NPC469599
0.8333	Intermediate Similarity	NPC271195

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 NPC472932 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1395
0.2-0.3	3978
0.3-0.4	2534
0.4-0.5	614
0.5-0.6	170
0.6-0.7	152
0.7-0.8	137
0.8-0.85	25
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8652	High Similarity	NPD3665	Phase 1
0.8652	High Similarity	NPD3133	Approved
0.8652	High Similarity	NPD3666	Approved
0.8587	High Similarity	NPD5328	Approved
0.8587	High Similarity	NPD4753	Phase 2
0.8571	High Similarity	NPD5211	Phase 2
0.8542	High Similarity	NPD4755	Approved
0.8444	Intermediate Similarity	NPD4786	Approved
0.8404	Intermediate Similarity	NPD6079	Approved
0.84	Intermediate Similarity	NPD5141	Approved
0.8367	Intermediate Similarity	NPD4696	Approved
0.8367	Intermediate Similarity	NPD4700	Approved
0.8367	Intermediate Similarity	NPD5286	Approved
0.8367	Intermediate Similarity	NPD5285	Approved
0.8261	Intermediate Similarity	NPD5279	Phase 3
0.8222	Intermediate Similarity	NPD4221	Approved
0.8222	Intermediate Similarity	NPD3667	Approved
0.8222	Intermediate Similarity	NPD4223	Phase 3
0.82	Intermediate Similarity	NPD4633	Approved
0.82	Intermediate Similarity	NPD5225	Approved
0.82	Intermediate Similarity	NPD5224	Approved
0.82	Intermediate Similarity	NPD5226	Approved
0.8163	Intermediate Similarity	NPD6084	Phase 2
0.8163	Intermediate Similarity	NPD6083	Phase 2
0.8152	Intermediate Similarity	NPD5329	Approved
0.8144	Intermediate Similarity	NPD4629	Approved
0.8144	Intermediate Similarity	NPD5695	Phase 3
0.8144	Intermediate Similarity	NPD5210	Approved
0.8137	Intermediate Similarity	NPD7128	Approved
0.8137	Intermediate Similarity	NPD5739	Approved
0.8137	Intermediate Similarity	NPD6675	Approved
0.8137	Intermediate Similarity	NPD6402	Approved
0.8125	Intermediate Similarity	NPD4202	Approved
0.8119	Intermediate Similarity	NPD5175	Approved
0.8119	Intermediate Similarity	NPD5174	Approved
0.81	Intermediate Similarity	NPD5223	Approved
0.8065	Intermediate Similarity	NPD5280	Approved
0.8065	Intermediate Similarity	NPD3618	Phase 1
0.8065	Intermediate Similarity	NPD5690	Phase 2
0.8065	Intermediate Similarity	NPD4694	Approved
0.8061	Intermediate Similarity	NPD5222	Approved
0.8061	Intermediate Similarity	NPD5221	Approved
0.8061	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD4697	Phase 3
0.8043	Intermediate Similarity	NPD4197	Approved
0.7981	Intermediate Similarity	NPD6881	Approved
0.7981	Intermediate Similarity	NPD6899	Approved
0.7981	Intermediate Similarity	NPD7320	Approved
0.798	Intermediate Similarity	NPD5173	Approved
0.7961	Intermediate Similarity	NPD4767	Approved
0.7961	Intermediate Similarity	NPD4768	Approved
0.7941	Intermediate Similarity	NPD4754	Approved
0.7905	Intermediate Similarity	NPD6372	Approved
0.7905	Intermediate Similarity	NPD6373	Approved
0.7885	Intermediate Similarity	NPD5697	Approved
0.7885	Intermediate Similarity	NPD5701	Approved
0.7872	Intermediate Similarity	NPD4689	Approved
0.7872	Intermediate Similarity	NPD5205	Approved
0.7872	Intermediate Similarity	NPD4138	Approved
0.7872	Intermediate Similarity	NPD7521	Approved
0.7872	Intermediate Similarity	NPD7334	Approved
0.7872	Intermediate Similarity	NPD4690	Approved
0.7872	Intermediate Similarity	NPD6409	Approved
0.7872	Intermediate Similarity	NPD4688	Approved
0.7872	Intermediate Similarity	NPD7146	Approved
0.7872	Intermediate Similarity	NPD5330	Approved
0.7872	Intermediate Similarity	NPD4693	Phase 3
0.7872	Intermediate Similarity	NPD6684	Approved
0.7835	Intermediate Similarity	NPD5284	Approved
0.7835	Intermediate Similarity	NPD5281	Approved
0.783	Intermediate Similarity	NPD7102	Approved
0.783	Intermediate Similarity	NPD6883	Approved
0.783	Intermediate Similarity	NPD7290	Approved
0.781	Intermediate Similarity	NPD5128	Approved
0.781	Intermediate Similarity	NPD4730	Approved
0.781	Intermediate Similarity	NPD4729	Approved
0.7757	Intermediate Similarity	NPD6869	Approved
0.7757	Intermediate Similarity	NPD6617	Approved
0.7757	Intermediate Similarity	NPD6847	Approved
0.7757	Intermediate Similarity	NPD6649	Approved
0.7757	Intermediate Similarity	NPD6650	Approved
0.7757	Intermediate Similarity	NPD8130	Phase 1
0.7755	Intermediate Similarity	NPD6399	Phase 3
0.7742	Intermediate Similarity	NPD4788	Approved
0.7736	Intermediate Similarity	NPD6012	Approved
0.7736	Intermediate Similarity	NPD6014	Approved
0.7736	Intermediate Similarity	NPD6013	Approved
0.7723	Intermediate Similarity	NPD5696	Approved
0.7708	Intermediate Similarity	NPD6903	Approved
0.7708	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6882	Approved
0.7685	Intermediate Similarity	NPD8297	Approved
0.7664	Intermediate Similarity	NPD5247	Approved
0.7664	Intermediate Similarity	NPD5251	Approved
0.7664	Intermediate Similarity	NPD4634	Approved
0.7664	Intermediate Similarity	NPD5250	Approved
0.7664	Intermediate Similarity	NPD5249	Phase 3
0.7664	Intermediate Similarity	NPD5248	Approved
0.766	Intermediate Similarity	NPD3668	Phase 3
0.7642	Intermediate Similarity	NPD6011	Approved
0.7593	Intermediate Similarity	NPD5215	Approved
0.7593	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5216	Approved
0.7593	Intermediate Similarity	NPD5217	Approved
0.7556	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4096	Approved
0.7547	Intermediate Similarity	NPD6412	Phase 2
0.7527	Intermediate Similarity	NPD4692	Approved
0.7527	Intermediate Similarity	NPD4139	Approved
0.7526	Intermediate Similarity	NPD6672	Approved
0.7526	Intermediate Similarity	NPD5737	Approved
0.7526	Intermediate Similarity	NPD4518	Approved
0.7523	Intermediate Similarity	NPD6053	Discontinued
0.75	Intermediate Similarity	NPD4623	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4519	Discontinued
0.75	Intermediate Similarity	NPD5169	Approved
0.75	Intermediate Similarity	NPD5135	Approved
0.75	Intermediate Similarity	NPD4195	Approved
0.7476	Intermediate Similarity	NPD7640	Approved
0.7476	Intermediate Similarity	NPD7639	Approved
0.7475	Intermediate Similarity	NPD7515	Phase 2
0.7475	Intermediate Similarity	NPD6050	Approved
0.7449	Intermediate Similarity	NPD6673	Approved
0.7449	Intermediate Similarity	NPD6080	Approved
0.7449	Intermediate Similarity	NPD6904	Approved
0.7444	Intermediate Similarity	NPD7339	Approved
0.7444	Intermediate Similarity	NPD6942	Approved
0.7431	Intermediate Similarity	NPD5127	Approved
0.7423	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4695	Discontinued
0.7411	Intermediate Similarity	NPD7115	Discovery
0.74	Intermediate Similarity	NPD5133	Approved
0.7396	Intermediate Similarity	NPD5363	Approved
0.7391	Intermediate Similarity	NPD3617	Approved
0.7391	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7638	Approved
0.7374	Intermediate Similarity	NPD5692	Phase 3
0.7374	Intermediate Similarity	NPD5785	Approved
0.7368	Intermediate Similarity	NPD5362	Discontinued
0.7333	Intermediate Similarity	NPD5733	Approved
0.7321	Intermediate Similarity	NPD6274	Approved
0.732	Intermediate Similarity	NPD5786	Approved
0.7315	Intermediate Similarity	NPD5168	Approved
0.73	Intermediate Similarity	NPD5694	Approved
0.73	Intermediate Similarity	NPD6411	Approved
0.73	Intermediate Similarity	NPD5693	Phase 1
0.7297	Intermediate Similarity	NPD4632	Approved
0.729	Intermediate Similarity	NPD6008	Approved
0.7281	Intermediate Similarity	NPD7101	Approved
0.7281	Intermediate Similarity	NPD7100	Approved
0.7263	Intermediate Similarity	NPD4269	Approved
0.7263	Intermediate Similarity	NPD4270	Approved
0.7255	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5368	Approved
0.7232	Intermediate Similarity	NPD5167	Approved
0.7228	Intermediate Similarity	NPD5778	Approved
0.7228	Intermediate Similarity	NPD5779	Approved
0.7217	Intermediate Similarity	NPD6054	Approved
0.7217	Intermediate Similarity	NPD6059	Approved
0.72	Intermediate Similarity	NPD5207	Approved
0.7193	Intermediate Similarity	NPD6335	Approved
0.7191	Intermediate Similarity	NPD4747	Approved
0.7172	Intermediate Similarity	NPD5208	Approved
0.7157	Intermediate Similarity	NPD7748	Approved
0.7155	Intermediate Similarity	NPD6909	Approved
0.7155	Intermediate Similarity	NPD6908	Approved
0.7143	Intermediate Similarity	NPD4687	Approved
0.7143	Intermediate Similarity	NPD6404	Discontinued
0.7143	Intermediate Similarity	NPD4785	Approved
0.7143	Intermediate Similarity	NPD4784	Approved
0.7143	Intermediate Similarity	NPD6098	Approved
0.7128	Intermediate Similarity	NPD6929	Approved
0.7111	Intermediate Similarity	NPD4243	Approved
0.7111	Intermediate Similarity	NPD5276	Approved
0.7105	Intermediate Similarity	NPD6009	Approved
0.7105	Intermediate Similarity	NPD6317	Approved
0.71	Intermediate Similarity	NPD6101	Approved
0.71	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6370	Approved
0.7083	Intermediate Similarity	NPD6435	Approved
0.7079	Intermediate Similarity	NPD4137	Phase 3
0.7069	Intermediate Similarity	NPD6319	Approved
0.7053	Intermediate Similarity	NPD4819	Approved
0.7053	Intermediate Similarity	NPD4822	Approved
0.7053	Intermediate Similarity	NPD4252	Approved
0.7053	Intermediate Similarity	NPD6930	Phase 2
0.7053	Intermediate Similarity	NPD6931	Approved
0.7053	Intermediate Similarity	NPD4821	Approved
0.7053	Intermediate Similarity	NPD7525	Registered
0.7053	Intermediate Similarity	NPD4748	Discontinued
0.7053	Intermediate Similarity	NPD4820	Approved
0.7043	Intermediate Similarity	NPD6313	Approved
0.7043	Intermediate Similarity	NPD6314	Approved
0.7041	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4268	Approved
0.7021	Intermediate Similarity	NPD4271	Approved
0.7018	Intermediate Similarity	NPD6868	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