NPASS Compound

Structure

CID271195 OpenBabel06191716072D 30 33 0 0 1 0 0 0 0 0999 V2000 -3.2500 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8973 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -1.9135 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 -2.6320 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 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 -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 -0.0000 -1.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9192 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -2.2601 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 -2.6831 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 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 2 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 -1.7321 -1.0000 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 0.2588 0.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 15 23 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 18 3 1 1 0 0 0 18 20 1 0 0 0 0 19 28 1 1 0 0 0 20 25 1 1 0 0 0 21 22 1 0 0 0 0 21 25 1 1 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 1 0 0 0 24 29 2 0 0 0 0 25 4 1 1 0 0 0 26 27 1 6 0 0 0 27 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.33
Volume:	462.42
LogP:	4.859
LogD:	5.029
LogS:	-5.3
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	4.793
Fsp3:	0.889
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:	-4.76
MDCK Permeability:	2.2312191504170187e-05
Pgp-inhibitor:	0.203
Pgp-substrate:	0.14
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.694
30% Bioavailability (F30%):	0.363

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.62
Plasma Protein Binding (PPB):	94.51092529296875%
Volume Distribution (VD):	1.387
Pgp-substrate:	1.4138846397399902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.361
CYP2C19-inhibitor:	0.321
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.46
CYP2C9-substrate:	0.137
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.874
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	9.079
Half-life (T1/2):	0.105

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.388
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.578
Carcinogencity:	0.199
Eye Corrosion:	0.526
Eye Irritation:	0.288
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC271195

Natural Product ID:	NPC271195
*Common Name:**	Viperidone
IUPAC Name:	(3S,5S,9S,10S,13R,14R,17R)-3,9-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:	Viperidone
Standard InCHIKey:	HGCLEPLEUUJGID-REBIDWDSSA-N
Standard InCHI:	InChI=1S/C27H44O3/c1-17(2)7-6-8-18(3)20-9-10-21-22-16-24(29)23-15-19(28)11-12-26(23,5)27(22,30)14-13-25(20,21)4/h16-21,23,28,30H,6-15H2,1-5H3/t18-,19+,20-,21+,23-,25-,26+,27-/m1/s1
SMILES:	CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@]1(C2=CC(=O)[C@@H]2[C@]1(C)CC[C@@H](C2)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470041
PubChem CID:	21593998
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
NPO15389	Ganoderma annulare	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12781809]
NPO3493	Crotalaria incana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3493	Crotalaria incana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2796	Coprinopsis episcopalis	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17853	Dorcoceras hygrometricum	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3493	Crotalaria incana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9297	Machilus edulis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16704	Aeollanthus rydingianus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15389	Ganoderma annulare	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2796	Coprinopsis episcopalis	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17928	Callophycus oppositifolius	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
EC50	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	LC50	=	100.0	nM	PMID[478343]
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	EC50	>	15000.0	nM	PMID[478343]

☑ 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 NPC271195 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	167
0.1-0.2	1127
0.2-0.3	4371
0.3-0.4	11223
0.4-0.5	10796
0.5-0.6	6297
0.6-0.7	5527
0.7-0.8	2757
0.8-0.85	293
0.85-0.9	116
0.9-0.95	18
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC154072
0.9457	High Similarity	NPC103051
0.9438	High Similarity	NPC475806
0.9438	High Similarity	NPC233116
0.9432	High Similarity	NPC473999
0.9432	High Similarity	NPC309603
0.9326	High Similarity	NPC48010
0.9263	High Similarity	NPC247957
0.9263	High Similarity	NPC249187
0.9231	High Similarity	NPC8993
0.9222	High Similarity	NPC473998
0.9167	High Similarity	NPC209502
0.9167	High Similarity	NPC204833
0.9167	High Similarity	NPC72255
0.913	High Similarity	NPC259286
0.9121	High Similarity	NPC69454
0.9101	High Similarity	NPC193360
0.9091	High Similarity	NPC472986
0.9091	High Similarity	NPC472985
0.9072	High Similarity	NPC150531
0.9072	High Similarity	NPC296945
0.9072	High Similarity	NPC149047
0.9072	High Similarity	NPC49958
0.9072	High Similarity	NPC48733
0.9072	High Similarity	NPC476027
0.9072	High Similarity	NPC214264
0.9072	High Similarity	NPC257353
0.9072	High Similarity	NPC171137
0.9072	High Similarity	NPC152695
0.9072	High Similarity	NPC85829
0.9072	High Similarity	NPC302607
0.9072	High Similarity	NPC319077
0.9072	High Similarity	NPC97202
0.9072	High Similarity	NPC202167
0.9072	High Similarity	NPC260268
0.9072	High Similarity	NPC50692
0.9032	High Similarity	NPC249954
0.9022	High Similarity	NPC196485
0.9022	High Similarity	NPC111015
0.9022	High Similarity	NPC245972
0.9011	High Similarity	NPC63748
0.9	High Similarity	NPC186688
0.8989	High Similarity	NPC475740
0.898	High Similarity	NPC220229
0.898	High Similarity	NPC475060
0.898	High Similarity	NPC477916
0.898	High Similarity	NPC83744
0.8977	High Similarity	NPC470574
0.8977	High Similarity	NPC471224
0.8958	High Similarity	NPC477915
0.8958	High Similarity	NPC293753
0.8958	High Similarity	NPC234892
0.8936	High Similarity	NPC320306
0.8925	High Similarity	NPC297199
0.8889	High Similarity	NPC471722
0.8889	High Similarity	NPC329417
0.8889	High Similarity	NPC328539
0.8889	High Similarity	NPC217201
0.8876	High Similarity	NPC145879
0.8876	High Similarity	NPC474778
0.8876	High Similarity	NPC474732
0.8876	High Similarity	NPC31564
0.8876	High Similarity	NPC474733
0.8876	High Similarity	NPC72133
0.8864	High Similarity	NPC85774
0.8864	High Similarity	NPC214043
0.8817	High Similarity	NPC299100
0.8817	High Similarity	NPC292793
0.8804	High Similarity	NPC272746
0.88	High Similarity	NPC11710
0.8791	High Similarity	NPC31985
0.8791	High Similarity	NPC2983
0.8791	High Similarity	NPC472973
0.8791	High Similarity	NPC1015
0.8791	High Similarity	NPC86319
0.8791	High Similarity	NPC119416
0.8791	High Similarity	NPC275740
0.8778	High Similarity	NPC58063
0.8764	High Similarity	NPC474083
0.875	High Similarity	NPC327431
0.8737	High Similarity	NPC108078
0.8737	High Similarity	NPC122294
0.8723	High Similarity	NPC180950
0.8713	High Similarity	NPC76084
0.871	High Similarity	NPC475255
0.871	High Similarity	NPC472930
0.871	High Similarity	NPC474736
0.871	High Similarity	NPC109305
0.8696	High Similarity	NPC191684
0.8696	High Similarity	NPC126993
0.8696	High Similarity	NPC85173
0.8687	High Similarity	NPC166607
0.8681	High Similarity	NPC131470
0.8681	High Similarity	NPC143767
0.8667	High Similarity	NPC469994
0.8652	High Similarity	NPC473246
0.8652	High Similarity	NPC221758
0.8652	High Similarity	NPC59453
0.8646	High Similarity	NPC16021
0.8632	High Similarity	NPC7124
0.8632	High Similarity	NPC117133
0.8617	High Similarity	NPC474690
0.8617	High Similarity	NPC209662
0.8617	High Similarity	NPC119562
0.8617	High Similarity	NPC279410
0.8602	High Similarity	NPC168027
0.8602	High Similarity	NPC131872
0.8602	High Similarity	NPC185936
0.8602	High Similarity	NPC116726
0.8602	High Similarity	NPC472978
0.8587	High Similarity	NPC262858
0.8587	High Similarity	NPC268406
0.8587	High Similarity	NPC32830
0.8587	High Similarity	NPC472971
0.8587	High Similarity	NPC474245
0.8587	High Similarity	NPC472240
0.8587	High Similarity	NPC26959
0.8587	High Similarity	NPC477943
0.8587	High Similarity	NPC472970
0.8586	High Similarity	NPC160843
0.8571	High Similarity	NPC141292
0.8571	High Similarity	NPC474684
0.8571	High Similarity	NPC142361
0.8571	High Similarity	NPC473424
0.8557	High Similarity	NPC144660
0.8557	High Similarity	NPC470074
0.8557	High Similarity	NPC299971
0.8557	High Similarity	NPC307954
0.8556	High Similarity	NPC474218
0.8556	High Similarity	NPC469948
0.8544	High Similarity	NPC207251
0.8542	High Similarity	NPC474938
0.8542	High Similarity	NPC126815
0.8542	High Similarity	NPC253826
0.8542	High Similarity	NPC474785
0.8526	High Similarity	NPC472485
0.8515	High Similarity	NPC65941
0.8511	High Similarity	NPC12722
0.85	High Similarity	NPC323834
0.8495	Intermediate Similarity	NPC183283
0.8495	Intermediate Similarity	NPC469400
0.8495	Intermediate Similarity	NPC320026
0.8485	Intermediate Similarity	NPC311612
0.8485	Intermediate Similarity	NPC36688
0.8485	Intermediate Similarity	NPC478057
0.8478	Intermediate Similarity	NPC472802
0.8478	Intermediate Similarity	NPC471724
0.8478	Intermediate Similarity	NPC310752
0.8478	Intermediate Similarity	NPC474677
0.8478	Intermediate Similarity	NPC292491
0.8469	Intermediate Similarity	NPC472924
0.8462	Intermediate Similarity	NPC6391
0.8462	Intermediate Similarity	NPC317210
0.8462	Intermediate Similarity	NPC472974
0.8462	Intermediate Similarity	NPC222613
0.8462	Intermediate Similarity	NPC261266
0.8462	Intermediate Similarity	NPC108721
0.8462	Intermediate Similarity	NPC472738
0.8462	Intermediate Similarity	NPC51014
0.8462	Intermediate Similarity	NPC94755
0.8462	Intermediate Similarity	NPC962
0.8462	Intermediate Similarity	NPC118648
0.8462	Intermediate Similarity	NPC73300
0.8462	Intermediate Similarity	NPC475022
0.8462	Intermediate Similarity	NPC250109
0.8454	Intermediate Similarity	NPC114274
0.8454	Intermediate Similarity	NPC191565
0.8444	Intermediate Similarity	NPC58841
0.8444	Intermediate Similarity	NPC161423
0.8444	Intermediate Similarity	NPC82902
0.8444	Intermediate Similarity	NPC227064
0.8444	Intermediate Similarity	NPC476412
0.8444	Intermediate Similarity	NPC472265
0.8444	Intermediate Similarity	NPC237712
0.8444	Intermediate Similarity	NPC329043
0.8444	Intermediate Similarity	NPC321187
0.8438	Intermediate Similarity	NPC471463
0.8438	Intermediate Similarity	NPC301534
0.8438	Intermediate Similarity	NPC49371
0.8438	Intermediate Similarity	NPC250757
0.8438	Intermediate Similarity	NPC192428
0.8438	Intermediate Similarity	NPC472941
0.8438	Intermediate Similarity	NPC456
0.8431	Intermediate Similarity	NPC214644
0.8427	Intermediate Similarity	NPC151519
0.8421	Intermediate Similarity	NPC472977
0.8421	Intermediate Similarity	NPC472976
0.8421	Intermediate Similarity	NPC471207
0.8421	Intermediate Similarity	NPC196227
0.8421	Intermediate Similarity	NPC469406
0.8416	Intermediate Similarity	NPC472925
0.8416	Intermediate Similarity	NPC185
0.8409	Intermediate Similarity	NPC172013
0.8404	Intermediate Similarity	NPC86266
0.8404	Intermediate Similarity	NPC110657
0.8404	Intermediate Similarity	NPC73457
0.8404	Intermediate Similarity	NPC472975
0.8404	Intermediate Similarity	NPC212301
0.8387	Intermediate Similarity	NPC146554
0.8387	Intermediate Similarity	NPC472983

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 NPC271195 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1431
0.2-0.3	3931
0.3-0.4	2454
0.4-0.5	688
0.5-0.6	162
0.6-0.7	129
0.7-0.8	163
0.8-0.85	33
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD3618	Phase 1
0.9	High Similarity	NPD5328	Approved
0.8804	High Similarity	NPD6079	Approved
0.871	High Similarity	NPD4202	Approved
0.8652	High Similarity	NPD4786	Approved
0.8444	Intermediate Similarity	NPD3665	Phase 1
0.8444	Intermediate Similarity	NPD3666	Approved
0.8444	Intermediate Similarity	NPD3133	Approved
0.8438	Intermediate Similarity	NPD4697	Phase 3
0.8427	Intermediate Similarity	NPD3667	Approved
0.8384	Intermediate Similarity	NPD5211	Phase 2
0.8351	Intermediate Similarity	NPD4755	Approved
0.8247	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD5221	Approved
0.8247	Intermediate Similarity	NPD5222	Approved
0.8222	Intermediate Similarity	NPD4221	Approved
0.8222	Intermediate Similarity	NPD4223	Phase 3
0.8218	Intermediate Similarity	NPD5141	Approved
0.8191	Intermediate Similarity	NPD4753	Phase 2
0.8182	Intermediate Similarity	NPD5286	Approved
0.8182	Intermediate Similarity	NPD5285	Approved
0.8182	Intermediate Similarity	NPD4700	Approved
0.8182	Intermediate Similarity	NPD4696	Approved
0.8182	Intermediate Similarity	NPD7640	Approved
0.8182	Intermediate Similarity	NPD7639	Approved
0.8163	Intermediate Similarity	NPD5173	Approved
0.8152	Intermediate Similarity	NPD5329	Approved
0.81	Intermediate Similarity	NPD5223	Approved
0.8081	Intermediate Similarity	NPD7638	Approved
0.8065	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD5279	Phase 3
0.8043	Intermediate Similarity	NPD4197	Approved
0.8021	Intermediate Similarity	NPD7515	Phase 2
0.802	Intermediate Similarity	NPD4633	Approved
0.802	Intermediate Similarity	NPD5225	Approved
0.802	Intermediate Similarity	NPD5226	Approved
0.802	Intermediate Similarity	NPD5224	Approved
0.7961	Intermediate Similarity	NPD6402	Approved
0.7961	Intermediate Similarity	NPD7128	Approved
0.7961	Intermediate Similarity	NPD5739	Approved
0.7961	Intermediate Similarity	NPD6675	Approved
0.7959	Intermediate Similarity	NPD5210	Approved
0.7959	Intermediate Similarity	NPD4629	Approved
0.7941	Intermediate Similarity	NPD5175	Approved
0.7941	Intermediate Similarity	NPD4754	Approved
0.7941	Intermediate Similarity	NPD5174	Approved
0.7938	Intermediate Similarity	NPD6399	Phase 3
0.7905	Intermediate Similarity	NPD6373	Approved
0.7905	Intermediate Similarity	NPD6372	Approved
0.789	Intermediate Similarity	NPD7115	Discovery
0.7872	Intermediate Similarity	NPD4689	Approved
0.7872	Intermediate Similarity	NPD4623	Approved
0.7872	Intermediate Similarity	NPD4138	Approved
0.7872	Intermediate Similarity	NPD4519	Discontinued
0.7872	Intermediate Similarity	NPD4690	Approved
0.7872	Intermediate Similarity	NPD5205	Approved
0.7872	Intermediate Similarity	NPD4688	Approved
0.7872	Intermediate Similarity	NPD4693	Phase 3
0.783	Intermediate Similarity	NPD4634	Approved
0.781	Intermediate Similarity	NPD6881	Approved
0.781	Intermediate Similarity	NPD6899	Approved
0.781	Intermediate Similarity	NPD7320	Approved
0.7802	Intermediate Similarity	NPD7525	Registered
0.78	Intermediate Similarity	NPD6083	Phase 2
0.78	Intermediate Similarity	NPD6084	Phase 2
0.7789	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD4767	Approved
0.7788	Intermediate Similarity	NPD4768	Approved
0.7766	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD6649	Approved
0.7757	Intermediate Similarity	NPD6650	Approved
0.7742	Intermediate Similarity	NPD4788	Approved
0.7714	Intermediate Similarity	NPD5701	Approved
0.7714	Intermediate Similarity	NPD5697	Approved
0.7684	Intermediate Similarity	NPD7521	Approved
0.7684	Intermediate Similarity	NPD7334	Approved
0.7684	Intermediate Similarity	NPD6684	Approved
0.7684	Intermediate Similarity	NPD5690	Phase 2
0.7684	Intermediate Similarity	NPD5280	Approved
0.7684	Intermediate Similarity	NPD7146	Approved
0.7684	Intermediate Similarity	NPD5330	Approved
0.7684	Intermediate Similarity	NPD4694	Approved
0.7684	Intermediate Similarity	NPD6409	Approved
0.7677	Intermediate Similarity	NPD7748	Approved
0.7664	Intermediate Similarity	NPD7102	Approved
0.7664	Intermediate Similarity	NPD7290	Approved
0.7664	Intermediate Similarity	NPD6883	Approved
0.766	Intermediate Similarity	NPD3668	Phase 3
0.7642	Intermediate Similarity	NPD5128	Approved
0.7642	Intermediate Similarity	NPD4729	Approved
0.7642	Intermediate Similarity	NPD4730	Approved
0.7642	Intermediate Similarity	NPD6011	Approved
0.764	Intermediate Similarity	NPD7339	Approved
0.764	Intermediate Similarity	NPD6942	Approved
0.7624	Intermediate Similarity	NPD7902	Approved
0.7619	Intermediate Similarity	NPD6008	Approved
0.7615	Intermediate Similarity	NPD4632	Approved
0.76	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD8130	Phase 1
0.7593	Intermediate Similarity	NPD6847	Approved
0.7593	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6617	Approved
0.7593	Intermediate Similarity	NPD6869	Approved
0.7582	Intermediate Similarity	NPD3617	Approved
0.757	Intermediate Similarity	NPD6014	Approved
0.757	Intermediate Similarity	NPD6012	Approved
0.757	Intermediate Similarity	NPD6013	Approved
0.7549	Intermediate Similarity	NPD5696	Approved
0.7526	Intermediate Similarity	NPD6903	Approved
0.7526	Intermediate Similarity	NPD6672	Approved
0.7526	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5737	Approved
0.7523	Intermediate Similarity	NPD6882	Approved
0.7523	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD5248	Approved
0.75	Intermediate Similarity	NPD5247	Approved
0.75	Intermediate Similarity	NPD7632	Discontinued
0.75	Intermediate Similarity	NPD5250	Approved
0.75	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5249	Phase 3
0.75	Intermediate Similarity	NPD4195	Approved
0.75	Intermediate Similarity	NPD5169	Approved
0.75	Intermediate Similarity	NPD5251	Approved
0.75	Intermediate Similarity	NPD5135	Approved
0.7477	Intermediate Similarity	NPD5168	Approved
0.7475	Intermediate Similarity	NPD5281	Approved
0.7475	Intermediate Similarity	NPD5284	Approved
0.7431	Intermediate Similarity	NPD5127	Approved
0.7431	Intermediate Similarity	NPD5216	Approved
0.7431	Intermediate Similarity	NPD5215	Approved
0.7431	Intermediate Similarity	NPD5217	Approved
0.7426	Intermediate Similarity	NPD5695	Phase 3
0.7419	Intermediate Similarity	NPD6931	Approved
0.7419	Intermediate Similarity	NPD6930	Phase 2
0.7411	Intermediate Similarity	NPD6009	Approved
0.7386	Intermediate Similarity	NPD4747	Approved
0.7383	Intermediate Similarity	NPD6412	Phase 2
0.7368	Intermediate Similarity	NPD6054	Approved
0.7368	Intermediate Similarity	NPD6059	Approved
0.7363	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7900	Approved
0.7327	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6001	Approved
0.7312	Intermediate Similarity	NPD6929	Approved
0.7303	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD8035	Phase 2
0.73	Intermediate Similarity	NPD8034	Phase 2
0.7273	Intermediate Similarity	NPD6673	Approved
0.7273	Intermediate Similarity	NPD6080	Approved
0.7273	Intermediate Similarity	NPD6904	Approved
0.7273	Intermediate Similarity	NPD4137	Phase 3
0.7253	Intermediate Similarity	NPD3703	Phase 2
0.7241	Intermediate Similarity	NPD6370	Approved
0.7234	Intermediate Similarity	NPD4695	Discontinued
0.7234	Intermediate Similarity	NPD7514	Phase 3
0.7232	Intermediate Similarity	NPD5167	Approved
0.7217	Intermediate Similarity	NPD6319	Approved
0.7204	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6115	Approved
0.7204	Intermediate Similarity	NPD6114	Approved
0.7204	Intermediate Similarity	NPD6697	Approved
0.7204	Intermediate Similarity	NPD6118	Approved
0.72	Intermediate Similarity	NPD4096	Approved
0.7193	Intermediate Similarity	NPD6335	Approved
0.7191	Intermediate Similarity	NPD4691	Approved
0.7188	Intermediate Similarity	NPD6695	Phase 3
0.7179	Intermediate Similarity	NPD7604	Phase 2
0.7172	Intermediate Similarity	NPD5208	Approved
0.7168	Intermediate Similarity	NPD6274	Approved
0.7168	Intermediate Similarity	NPD6868	Approved
0.7158	Intermediate Similarity	NPD4692	Approved
0.7158	Intermediate Similarity	NPD4139	Approved
0.7155	Intermediate Similarity	NPD5983	Phase 2
0.7155	Intermediate Similarity	NPD6015	Approved
0.7155	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD6926	Approved
0.7143	Intermediate Similarity	NPD6924	Approved
0.7143	Intermediate Similarity	NPD5733	Approved
0.7143	Intermediate Similarity	NPD6098	Approved
0.713	Intermediate Similarity	NPD7101	Approved
0.713	Intermediate Similarity	NPD7100	Approved
0.7129	Intermediate Similarity	NPD5693	Phase 1
0.7128	Intermediate Similarity	NPD7645	Phase 2
0.7119	Intermediate Similarity	NPD7492	Approved
0.7113	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4243	Approved
0.7105	Intermediate Similarity	NPD6317	Approved
0.7097	Intermediate Similarity	NPD6925	Approved
0.7097	Intermediate Similarity	NPD5776	Phase 2
0.7094	Intermediate Similarity	NPD5988	Approved
0.7091	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3573	Approved
0.7059	Intermediate Similarity	NPD7507	Approved
0.7059	Intermediate Similarity	NPD6616	Approved
0.7059	Intermediate Similarity	NPD6336	Discontinued
0.7059	Intermediate Similarity	NPD5133	Approved
0.7053	Intermediate Similarity	NPD7332	Phase 2

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