NPASS Compound

Structure

NPC472930 OpenBabel07101718312D 35 38 0 0 1 0 0 0 0 0999 V2000 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 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 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 2.5385 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3435 1.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7036 3.0737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0345 2.3305 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 0.8660 -2.5000 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 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 1.6744 0.6363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6818 2.8658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 21 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 30 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 6 0 0 0 18 20 1 0 0 0 0 20 30 1 6 0 0 0 21 26 1 0 0 0 0 21 33 1 6 0 0 0 22 25 1 0 0 0 0 22 34 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 35 2 0 0 0 0 25 26 2 0 0 0 0 25 28 1 0 0 0 0 26 29 1 0 0 0 0 28 4 1 6 0 0 0 29 30 1 1 0 0 0 30 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	526.615
LogP:	3.764
LogD:	3.872
LogS:	-4.218
# Rotatable Bonds:	6
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.52
Synthetic Accessibility Score:	5.036
Fsp3:	0.833
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:	-4.993
MDCK Permeability:	1.1800343600043561e-05
Pgp-inhibitor:	0.646
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.553
Plasma Protein Binding (PPB):	80.5066909790039%
Volume Distribution (VD):	0.606
Pgp-substrate:	8.843057632446289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.308
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.129
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.557

ADMET: Excretion

Clearance (CL):	5.902
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.388
Skin Sensitization:	0.05
Carcinogencity:	0.132
Eye Corrosion:	0.028
Eye Irritation:	0.073
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC472930

Natural Product ID:	NPC472930
*Common Name:**	QDYKZRXXERLQAX-CBKWXKALSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QDYKZRXXERLQAX-CBKWXKALSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-18(8-7-9-19(16-31)17-32)20-10-13-29(5)26-21(33)14-23-27(2,3)24(35)11-12-28(23,4)25(26)22(34)15-30(20,29)6/h9,18,20-21,23,31-33H,7-8,10-17H2,1-6H3/t18-,20-,21+,23+,28+,29+,30-/m1/s1
SMILES:	CC(CCC=C(CO)CO)C1CCC2(C1(CC(=O)C3=C2C(CC4C3(CCC(=O)C4(C)C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594148
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[491385]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	11400.0	nM	PMID[491385]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	132400.0	nM	PMID[491385]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[491385]

☑ 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 NPC472930 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	155
0.1-0.2	1017
0.2-0.3	4623
0.3-0.4	11600
0.4-0.5	11068
0.5-0.6	6750
0.6-0.7	5294
0.7-0.8	1776
0.8-0.85	282
0.85-0.9	100
0.9-0.95	29
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9551	High Similarity	NPC472932
0.9545	High Similarity	NPC69454
0.9444	High Similarity	NPC249954
0.9432	High Similarity	NPC63748
0.9333	High Similarity	NPC469995
0.9333	High Similarity	NPC173875
0.9333	High Similarity	NPC174948
0.9333	High Similarity	NPC259286
0.9333	High Similarity	NPC318282
0.9231	High Similarity	NPC328371
0.9205	High Similarity	NPC275740
0.9205	High Similarity	NPC86319
0.9205	High Similarity	NPC123912
0.9186	High Similarity	NPC474083
0.914	High Similarity	NPC287833
0.914	High Similarity	NPC51370
0.9101	High Similarity	NPC48010
0.9091	High Similarity	NPC131470
0.9091	High Similarity	NPC143767
0.907	High Similarity	NPC473246
0.9043	High Similarity	NPC472924
0.9032	High Similarity	NPC197386
0.9032	High Similarity	NPC471717
0.9022	High Similarity	NPC472941
0.9022	High Similarity	NPC456
0.9011	High Similarity	NPC184870
0.9	High Similarity	NPC473998
0.9	High Similarity	NPC233116
0.8989	High Similarity	NPC309603
0.8989	High Similarity	NPC214387
0.8989	High Similarity	NPC473999
0.8989	High Similarity	NPC1015
0.8989	High Similarity	NPC31985
0.8966	High Similarity	NPC471224
0.8947	High Similarity	NPC204450
0.8947	High Similarity	NPC195290
0.8947	High Similarity	NPC473424
0.8913	High Similarity	NPC37646
0.8901	High Similarity	NPC472942
0.8889	High Similarity	NPC477149
0.8889	High Similarity	NPC477147
0.8889	High Similarity	NPC183283
0.8876	High Similarity	NPC471722
0.8876	High Similarity	NPC328539
0.8864	High Similarity	NPC72133
0.8854	High Similarity	NPC236390
0.8854	High Similarity	NPC111323
0.8851	High Similarity	NPC85774
0.8851	High Similarity	NPC214043
0.8842	High Similarity	NPC163372
0.8842	High Similarity	NPC302537
0.8817	High Similarity	NPC3772
0.8817	High Similarity	NPC243525
0.8817	High Similarity	NPC40765
0.8804	High Similarity	NPC8993
0.8804	High Similarity	NPC166906
0.8791	High Similarity	NPC472978
0.8791	High Similarity	NPC168027
0.8791	High Similarity	NPC475806
0.8791	High Similarity	NPC107690
0.8791	High Similarity	NPC185936
0.8778	High Similarity	NPC477943
0.8764	High Similarity	NPC475740
0.875	High Similarity	NPC472940
0.875	High Similarity	NPC87351
0.875	High Similarity	NPC308726
0.875	High Similarity	NPC119601
0.875	High Similarity	NPC472931
0.875	High Similarity	NPC477915
0.875	High Similarity	NPC469948
0.8723	High Similarity	NPC320306
0.8723	High Similarity	NPC121339
0.8723	High Similarity	NPC106557
0.8723	High Similarity	NPC18319
0.871	High Similarity	NPC317586
0.871	High Similarity	NPC271195
0.871	High Similarity	NPC470016
0.8696	High Similarity	NPC474736
0.8696	High Similarity	NPC470254
0.8696	High Similarity	NPC477520
0.8681	High Similarity	NPC191684
0.8681	High Similarity	NPC69622
0.866	High Similarity	NPC311612
0.8652	High Similarity	NPC474732
0.8652	High Similarity	NPC118648
0.8652	High Similarity	NPC469994
0.8652	High Similarity	NPC474733
0.8652	High Similarity	NPC31564
0.8652	High Similarity	NPC145879
0.8652	High Similarity	NPC222613
0.8652	High Similarity	NPC475022
0.8652	High Similarity	NPC474778
0.8632	High Similarity	NPC166745
0.8632	High Similarity	NPC10364
0.8632	High Similarity	NPC235464
0.8617	High Similarity	NPC471463
0.8617	High Similarity	NPC305483
0.8617	High Similarity	NPC328162
0.8617	High Similarity	NPC96859
0.8617	High Similarity	NPC117133
0.8602	High Similarity	NPC469406
0.8602	High Similarity	NPC474690
0.8587	High Similarity	NPC19114
0.8586	High Similarity	NPC83744
0.8586	High Similarity	NPC472925
0.8586	High Similarity	NPC185
0.8586	High Similarity	NPC477916
0.8571	High Similarity	NPC2983
0.8571	High Similarity	NPC209502
0.8571	High Similarity	NPC186688
0.8571	High Similarity	NPC204833
0.8571	High Similarity	NPC472973
0.8557	High Similarity	NPC293753
0.8557	High Similarity	NPC234892
0.8556	High Similarity	NPC136548
0.8556	High Similarity	NPC90652
0.8556	High Similarity	NPC317590
0.8556	High Similarity	NPC58063
0.8556	High Similarity	NPC287079
0.8542	High Similarity	NPC474720
0.8542	High Similarity	NPC205899
0.8542	High Similarity	NPC327431
0.8542	High Similarity	NPC476274
0.8542	High Similarity	NPC154072
0.8539	High Similarity	NPC470574
0.8526	High Similarity	NPC18509
0.8523	High Similarity	NPC476082
0.8523	High Similarity	NPC278648
0.8523	High Similarity	NPC41539
0.8511	High Similarity	NPC476174
0.8511	High Similarity	NPC473170
0.8511	High Similarity	NPC297199
0.8511	High Similarity	NPC180950
0.85	High Similarity	NPC295244
0.85	High Similarity	NPC329417
0.85	High Similarity	NPC65941
0.8495	Intermediate Similarity	NPC475255
0.8485	Intermediate Similarity	NPC149047
0.8485	Intermediate Similarity	NPC60681
0.8485	Intermediate Similarity	NPC48733
0.8485	Intermediate Similarity	NPC296945
0.8485	Intermediate Similarity	NPC260268
0.8485	Intermediate Similarity	NPC171137
0.8485	Intermediate Similarity	NPC323834
0.8485	Intermediate Similarity	NPC152695
0.8485	Intermediate Similarity	NPC50692
0.8485	Intermediate Similarity	NPC319077
0.8485	Intermediate Similarity	NPC302607
0.8485	Intermediate Similarity	NPC85829
0.8485	Intermediate Similarity	NPC476027
0.8485	Intermediate Similarity	NPC97202
0.8485	Intermediate Similarity	NPC49958
0.8485	Intermediate Similarity	NPC150531
0.8485	Intermediate Similarity	NPC214264
0.8485	Intermediate Similarity	NPC202167
0.8478	Intermediate Similarity	NPC129913
0.8478	Intermediate Similarity	NPC134321
0.8478	Intermediate Similarity	NPC320026
0.8478	Intermediate Similarity	NPC469400
0.8469	Intermediate Similarity	NPC26478
0.8469	Intermediate Similarity	NPC247957
0.8469	Intermediate Similarity	NPC249187
0.8462	Intermediate Similarity	NPC44181
0.8462	Intermediate Similarity	NPC471724
0.8462	Intermediate Similarity	NPC470417
0.8462	Intermediate Similarity	NPC53911
0.8454	Intermediate Similarity	NPC224720
0.8454	Intermediate Similarity	NPC476240
0.8454	Intermediate Similarity	NPC476223
0.8444	Intermediate Similarity	NPC472974
0.8444	Intermediate Similarity	NPC327115
0.8444	Intermediate Similarity	NPC94755
0.8438	Intermediate Similarity	NPC147954
0.8438	Intermediate Similarity	NPC103051
0.8427	Intermediate Similarity	NPC161423
0.8427	Intermediate Similarity	NPC165064
0.8427	Intermediate Similarity	NPC82902
0.8427	Intermediate Similarity	NPC227064
0.8427	Intermediate Similarity	NPC58841
0.8427	Intermediate Similarity	NPC476412
0.8427	Intermediate Similarity	NPC321187
0.8427	Intermediate Similarity	NPC227132
0.8427	Intermediate Similarity	NPC59453
0.8427	Intermediate Similarity	NPC221758
0.8427	Intermediate Similarity	NPC329043
0.8427	Intermediate Similarity	NPC237712
0.8421	Intermediate Similarity	NPC192428
0.8421	Intermediate Similarity	NPC7124
0.8416	Intermediate Similarity	NPC214644
0.8409	Intermediate Similarity	NPC311092
0.8404	Intermediate Similarity	NPC111015
0.8404	Intermediate Similarity	NPC473162
0.8404	Intermediate Similarity	NPC196485
0.8404	Intermediate Similarity	NPC472977
0.8404	Intermediate Similarity	NPC292793
0.8404	Intermediate Similarity	NPC473172
0.8404	Intermediate Similarity	NPC245972
0.8404	Intermediate Similarity	NPC472976
0.8404	Intermediate Similarity	NPC299100
0.84	Intermediate Similarity	NPC220229

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 NPC472930 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1363
0.2-0.3	3986
0.3-0.4	2526
0.4-0.5	647
0.5-0.6	176
0.6-0.7	160
0.7-0.8	130
0.8-0.85	20
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8989	High Similarity	NPD5328	Approved
0.8791	High Similarity	NPD6079	Approved
0.8557	High Similarity	NPD5211	Phase 2
0.8526	High Similarity	NPD4755	Approved
0.8444	Intermediate Similarity	NPD5279	Phase 3
0.8444	Intermediate Similarity	NPD3618	Phase 1
0.8427	Intermediate Similarity	NPD4786	Approved
0.8427	Intermediate Similarity	NPD3133	Approved
0.8427	Intermediate Similarity	NPD3665	Phase 1
0.8427	Intermediate Similarity	NPD3666	Approved
0.8421	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD5222	Approved
0.8421	Intermediate Similarity	NPD5221	Approved
0.8421	Intermediate Similarity	NPD4697	Phase 3
0.8384	Intermediate Similarity	NPD5141	Approved
0.837	Intermediate Similarity	NPD4753	Phase 2
0.8351	Intermediate Similarity	NPD4700	Approved
0.8351	Intermediate Similarity	NPD4696	Approved
0.8351	Intermediate Similarity	NPD5285	Approved
0.8351	Intermediate Similarity	NPD5286	Approved
0.8333	Intermediate Similarity	NPD5173	Approved
0.8202	Intermediate Similarity	NPD3667	Approved
0.8182	Intermediate Similarity	NPD5226	Approved
0.8182	Intermediate Similarity	NPD4633	Approved
0.8182	Intermediate Similarity	NPD5225	Approved
0.8182	Intermediate Similarity	NPD5224	Approved
0.8119	Intermediate Similarity	NPD5739	Approved
0.8119	Intermediate Similarity	NPD6675	Approved
0.8119	Intermediate Similarity	NPD7128	Approved
0.8119	Intermediate Similarity	NPD6402	Approved
0.8105	Intermediate Similarity	NPD4202	Approved
0.81	Intermediate Similarity	NPD5175	Approved
0.81	Intermediate Similarity	NPD5174	Approved
0.8081	Intermediate Similarity	NPD5223	Approved
0.8	Intermediate Similarity	NPD4221	Approved
0.8	Intermediate Similarity	NPD4223	Phase 3
0.7961	Intermediate Similarity	NPD7320	Approved
0.7961	Intermediate Similarity	NPD6899	Approved
0.7961	Intermediate Similarity	NPD6881	Approved
0.7959	Intermediate Similarity	NPD6084	Phase 2
0.7959	Intermediate Similarity	NPD6083	Phase 2
0.7941	Intermediate Similarity	NPD4767	Approved
0.7941	Intermediate Similarity	NPD4768	Approved
0.7938	Intermediate Similarity	NPD5210	Approved
0.7938	Intermediate Similarity	NPD4629	Approved
0.7938	Intermediate Similarity	NPD5695	Phase 3
0.7935	Intermediate Similarity	NPD5329	Approved
0.7921	Intermediate Similarity	NPD4754	Approved
0.7885	Intermediate Similarity	NPD6372	Approved
0.7885	Intermediate Similarity	NPD6373	Approved
0.7864	Intermediate Similarity	NPD5701	Approved
0.7864	Intermediate Similarity	NPD5697	Approved
0.7849	Intermediate Similarity	NPD5280	Approved
0.7849	Intermediate Similarity	NPD4694	Approved
0.7849	Intermediate Similarity	NPD5690	Phase 2
0.7826	Intermediate Similarity	NPD4197	Approved
0.7812	Intermediate Similarity	NPD7515	Phase 2
0.781	Intermediate Similarity	NPD7102	Approved
0.781	Intermediate Similarity	NPD6883	Approved
0.781	Intermediate Similarity	NPD7290	Approved
0.7788	Intermediate Similarity	NPD4730	Approved
0.7788	Intermediate Similarity	NPD4729	Approved
0.7788	Intermediate Similarity	NPD5128	Approved
0.7736	Intermediate Similarity	NPD6649	Approved
0.7736	Intermediate Similarity	NPD6847	Approved
0.7736	Intermediate Similarity	NPD6650	Approved
0.7736	Intermediate Similarity	NPD8130	Phase 1
0.7736	Intermediate Similarity	NPD6617	Approved
0.7736	Intermediate Similarity	NPD6869	Approved
0.7732	Intermediate Similarity	NPD6399	Phase 3
0.7714	Intermediate Similarity	NPD6012	Approved
0.7714	Intermediate Similarity	NPD6014	Approved
0.7714	Intermediate Similarity	NPD6013	Approved
0.7684	Intermediate Similarity	NPD6672	Approved
0.7684	Intermediate Similarity	NPD5737	Approved
0.7664	Intermediate Similarity	NPD6882	Approved
0.7664	Intermediate Similarity	NPD8297	Approved
0.766	Intermediate Similarity	NPD4689	Approved
0.766	Intermediate Similarity	NPD4690	Approved
0.766	Intermediate Similarity	NPD7334	Approved
0.766	Intermediate Similarity	NPD4693	Phase 3
0.766	Intermediate Similarity	NPD4623	Approved
0.766	Intermediate Similarity	NPD6409	Approved
0.766	Intermediate Similarity	NPD5205	Approved
0.766	Intermediate Similarity	NPD4688	Approved
0.766	Intermediate Similarity	NPD4138	Approved
0.766	Intermediate Similarity	NPD4519	Discontinued
0.766	Intermediate Similarity	NPD5330	Approved
0.766	Intermediate Similarity	NPD7146	Approved
0.766	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6684	Approved
0.766	Intermediate Similarity	NPD7521	Approved
0.7642	Intermediate Similarity	NPD5250	Approved
0.7642	Intermediate Similarity	NPD5249	Phase 3
0.7642	Intermediate Similarity	NPD5248	Approved
0.7642	Intermediate Similarity	NPD5247	Approved
0.7642	Intermediate Similarity	NPD5251	Approved
0.7642	Intermediate Similarity	NPD4634	Approved
0.7634	Intermediate Similarity	NPD3668	Phase 3
0.7629	Intermediate Similarity	NPD5281	Approved
0.7629	Intermediate Similarity	NPD5284	Approved
0.7624	Intermediate Similarity	NPD7640	Approved
0.7624	Intermediate Similarity	NPD7639	Approved
0.7619	Intermediate Similarity	NPD6011	Approved
0.7619	Intermediate Similarity	NPD5168	Approved
0.757	Intermediate Similarity	NPD5217	Approved
0.757	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD5216	Approved
0.757	Intermediate Similarity	NPD5215	Approved
0.7556	Intermediate Similarity	NPD3617	Approved
0.7556	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7115	Discovery
0.7527	Intermediate Similarity	NPD4788	Approved
0.7525	Intermediate Similarity	NPD7638	Approved
0.7525	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5733	Approved
0.7477	Intermediate Similarity	NPD5135	Approved
0.7477	Intermediate Similarity	NPD5169	Approved
0.7477	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7748	Approved
0.7416	Intermediate Similarity	NPD7339	Approved
0.7416	Intermediate Similarity	NPD6942	Approved
0.7407	Intermediate Similarity	NPD5127	Approved
0.7391	Intermediate Similarity	NPD4695	Discontinued
0.7391	Intermediate Similarity	NPD7525	Registered
0.7368	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6412	Phase 2
0.7356	Intermediate Similarity	NPD4747	Approved
0.7347	Intermediate Similarity	NPD4096	Approved
0.7312	Intermediate Similarity	NPD4139	Approved
0.7312	Intermediate Similarity	NPD4692	Approved
0.7303	Intermediate Similarity	NPD4687	Approved
0.7297	Intermediate Similarity	NPD6274	Approved
0.7297	Intermediate Similarity	NPD6868	Approved
0.7283	Intermediate Similarity	NPD4195	Approved
0.7282	Intermediate Similarity	NPD6404	Discontinued
0.7273	Intermediate Similarity	NPD4632	Approved
0.7273	Intermediate Similarity	NPD5276	Approved
0.7273	Intermediate Similarity	NPD6050	Approved
0.7273	Intermediate Similarity	NPD6411	Approved
0.7257	Intermediate Similarity	NPD7100	Approved
0.7257	Intermediate Similarity	NPD7101	Approved
0.7255	Intermediate Similarity	NPD7902	Approved
0.7245	Intermediate Similarity	NPD6673	Approved
0.7245	Intermediate Similarity	NPD6080	Approved
0.7245	Intermediate Similarity	NPD6904	Approved
0.7241	Intermediate Similarity	NPD4137	Phase 3
0.7228	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5167	Approved
0.72	Intermediate Similarity	NPD5133	Approved
0.72	Intermediate Similarity	NPD5779	Approved
0.72	Intermediate Similarity	NPD5778	Approved
0.7193	Intermediate Similarity	NPD6059	Approved
0.7193	Intermediate Similarity	NPD6054	Approved
0.7182	Intermediate Similarity	NPD6053	Discontinued
0.7172	Intermediate Similarity	NPD5692	Phase 3
0.7168	Intermediate Similarity	NPD6335	Approved
0.7159	Intermediate Similarity	NPD4691	Approved
0.7143	Intermediate Similarity	NPD4518	Approved
0.7143	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6909	Approved
0.713	Intermediate Similarity	NPD6908	Approved
0.7103	Intermediate Similarity	NPD6008	Approved
0.71	Intermediate Similarity	NPD5693	Phase 1
0.71	Intermediate Similarity	NPD5694	Approved
0.7097	Intermediate Similarity	NPD6929	Approved
0.708	Intermediate Similarity	NPD6009	Approved
0.708	Intermediate Similarity	NPD6317	Approved
0.7071	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6101	Approved
0.7071	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6370	Approved
0.7043	Intermediate Similarity	NPD6319	Approved
0.7041	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6931	Approved
0.7021	Intermediate Similarity	NPD5368	Approved
0.7021	Intermediate Similarity	NPD6930	Phase 2
0.7018	Intermediate Similarity	NPD6313	Approved
0.7018	Intermediate Similarity	NPD6314	Approved
0.701	Intermediate Similarity	NPD5363	Approved
0.7	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD5207	Approved
0.6983	Remote Similarity	NPD6015	Approved
0.6983	Remote Similarity	NPD6016	Approved
0.6981	Remote Similarity	NPD7632	Discontinued
0.6979	Remote Similarity	NPD5362	Discontinued
0.6979	Remote Similarity	NPD6695	Phase 3
0.697	Remote Similarity	NPD5208	Approved
0.6961	Remote Similarity	NPD7900	Approved
0.6961	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7492	Approved
0.6939	Remote Similarity	NPD6098	Approved
0.6939	Remote Similarity	NPD5786	Approved
0.6931	Remote Similarity	NPD8035	Phase 2
0.6931	Remote Similarity	NPD7637	Suspended
0.6931	Remote Similarity	NPD8034	Phase 2
0.6923	Remote Similarity	NPD4058	Approved
0.6923	Remote Similarity	NPD6926	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