NPASS Compound

Structure

CID76931 OpenBabel06191715412D 29 32 0 0 1 0 0 0 0 0999 V2000 -3.9961 6.3807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5373 5.6940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2031 4.6010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8066 3.7112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5343 2.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7443 3.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3479 3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 -1.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6888 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2220 1.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2217 0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8450 1.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6896 1.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5685 5.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1720 4.7026 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3790 2.9229 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0003 -0.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6882 -0.9747 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6891 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3787 1.9488 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5338 0.4869 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8447 0.4873 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5340 1.4614 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5544 -1.4744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 8 2 3 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 10 23 2 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 20 24 1 0 0 0 0 21 27 1 0 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 28 1 0 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.34
Volume:	459.499
LogP:	6.281
LogD:	5.737
LogS:	-6.794
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	4.631
Fsp3:	0.786
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:	-4.747
MDCK Permeability:	8.846444870869163e-06
Pgp-inhibitor:	0.982
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.511

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.62
Plasma Protein Binding (PPB):	99.84356689453125%
Volume Distribution (VD):	1.386
Pgp-substrate:	1.62714684009552%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.501
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.971
CYP2C9-inhibitor:	0.121
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.255
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	15.231
Half-life (T1/2):	0.028

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.01
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.474
Maximum Recommended Daily Dose:	0.612
Skin Sensitization:	0.077
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC76931

Natural Product ID:	NPC76931
*Common Name:**	17-(5,6-Dimethylhept-3-En-2-Yl)-10,13-Dimethyl-2,3,4,9,11,12,14,15,16,17-Decahydro-1H-Cyclopenta[A]Phenanthren-3-Ol
IUPAC Name:	17-(5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	DNVPQKQSNYMLRS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3
SMILES:	CC(C)C(C)C=CC(C)C1CCC2C3=CC=C4CC(CCC4(C)C3CCC12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3185842
PubChem CID:	247705
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[2082684]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21922656]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[3254039]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[3256207]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	twig	n.a.	PMID[9179367]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7808	Viscum album	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23218	Viscum coloratum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7808	Viscum album	Species	Viscaceae	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
Potency	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	26.6	nM	PMID[459956]

☑ 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 NPC76931 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	1188
0.2-0.3	5963
0.3-0.4	16189
0.4-0.5	8319
0.5-0.6	6033
0.6-0.7	3661
0.7-0.8	887
0.8-0.85	158
0.85-0.9	80
0.9-0.95	42
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC307965
1.0	High Similarity	NPC18603
0.9722	High Similarity	NPC113733
0.9583	High Similarity	NPC136188
0.9583	High Similarity	NPC285893
0.9583	High Similarity	NPC288035
0.9583	High Similarity	NPC134847
0.9583	High Similarity	NPC28657
0.9583	High Similarity	NPC304309
0.9583	High Similarity	NPC162742
0.9583	High Similarity	NPC22105
0.9583	High Similarity	NPC230301
0.9452	High Similarity	NPC240604
0.9452	High Similarity	NPC321381
0.9452	High Similarity	NPC134330
0.9452	High Similarity	NPC300324
0.9452	High Similarity	NPC321016
0.9452	High Similarity	NPC129165
0.9452	High Similarity	NPC107059
0.9324	High Similarity	NPC198968
0.9324	High Similarity	NPC155986
0.9324	High Similarity	NPC318495
0.9324	High Similarity	NPC34019
0.9315	High Similarity	NPC257347
0.9315	High Similarity	NPC141071
0.9315	High Similarity	NPC471468
0.9315	High Similarity	NPC471723
0.9211	High Similarity	NPC164840
0.9211	High Similarity	NPC209944
0.9211	High Similarity	NPC234193
0.9211	High Similarity	NPC241290
0.92	High Similarity	NPC477522
0.92	High Similarity	NPC186191
0.92	High Similarity	NPC474216
0.92	High Similarity	NPC473943
0.92	High Similarity	NPC87604
0.92	High Similarity	NPC205455
0.9189	High Similarity	NPC470362
0.9189	High Similarity	NPC189883
0.9091	High Similarity	NPC264245
0.9091	High Similarity	NPC47761
0.9079	High Similarity	NPC28862
0.9079	High Similarity	NPC47982
0.9079	High Similarity	NPC143182
0.9079	High Similarity	NPC84694
0.9079	High Similarity	NPC81306
0.9079	High Similarity	NPC328714
0.9079	High Similarity	NPC109546
0.9041	High Similarity	NPC471799
0.9028	High Similarity	NPC49422
0.9028	High Similarity	NPC9161
0.8987	High Similarity	NPC238485
0.8974	High Similarity	NPC201852
0.8974	High Similarity	NPC50964
0.8974	High Similarity	NPC49964
0.8961	High Similarity	NPC26117
0.8947	High Similarity	NPC318136
0.8947	High Similarity	NPC275910
0.8933	High Similarity	NPC237460
0.8933	High Similarity	NPC247325
0.8933	High Similarity	NPC244488
0.8933	High Similarity	NPC202642
0.8933	High Similarity	NPC96319
0.8933	High Similarity	NPC46160
0.8919	High Similarity	NPC471797
0.8919	High Similarity	NPC27395
0.8919	High Similarity	NPC329090
0.8889	High Similarity	NPC269877
0.8889	High Similarity	NPC167272
0.8861	High Similarity	NPC470384
0.8846	High Similarity	NPC474752
0.8846	High Similarity	NPC209620
0.8846	High Similarity	NPC470383
0.8846	High Similarity	NPC474759
0.8846	High Similarity	NPC474531
0.8846	High Similarity	NPC23852
0.8846	High Similarity	NPC82986
0.8846	High Similarity	NPC474731
0.8846	High Similarity	NPC474683
0.8846	High Similarity	NPC7505
0.8831	High Similarity	NPC30986
0.8831	High Similarity	NPC209430
0.8831	High Similarity	NPC1319
0.8816	High Similarity	NPC214570
0.88	High Similarity	NPC322353
0.88	High Similarity	NPC121744
0.88	High Similarity	NPC328104
0.88	High Similarity	NPC118508
0.88	High Similarity	NPC319090
0.8784	High Similarity	NPC474140
0.8784	High Similarity	NPC182717
0.8767	High Similarity	NPC145498
0.8767	High Similarity	NPC475728
0.875	High Similarity	NPC160209
0.875	High Similarity	NPC32055
0.875	High Similarity	NPC474493
0.875	High Similarity	NPC205845
0.875	High Similarity	NPC33913
0.875	High Similarity	NPC231310
0.875	High Similarity	NPC208999
0.8734	High Similarity	NPC189972
0.8734	High Similarity	NPC470614
0.8734	High Similarity	NPC1272
0.8734	High Similarity	NPC5985
0.8734	High Similarity	NPC101462
0.8734	High Similarity	NPC20853
0.8734	High Similarity	NPC202389
0.8718	High Similarity	NPC236112
0.8701	High Similarity	NPC285761
0.8701	High Similarity	NPC244385
0.8701	High Similarity	NPC6978
0.8701	High Similarity	NPC85346
0.8701	High Similarity	NPC65897
0.8701	High Similarity	NPC138621
0.8701	High Similarity	NPC302041
0.8701	High Similarity	NPC477514
0.8701	High Similarity	NPC167037
0.8684	High Similarity	NPC106432
0.8684	High Similarity	NPC315261
0.8684	High Similarity	NPC73875
0.8667	High Similarity	NPC243342
0.8667	High Similarity	NPC469534
0.8667	High Similarity	NPC477138
0.8667	High Similarity	NPC469533
0.8667	High Similarity	NPC469593
0.8649	High Similarity	NPC242001
0.8642	High Similarity	NPC157257
0.8642	High Similarity	NPC274448
0.8625	High Similarity	NPC475789
0.8625	High Similarity	NPC474634
0.8625	High Similarity	NPC317458
0.8611	High Similarity	NPC197805
0.8608	High Similarity	NPC6707
0.859	High Similarity	NPC273410
0.859	High Similarity	NPC80530
0.8571	High Similarity	NPC471798
0.8554	High Similarity	NPC470542
0.8553	High Similarity	NPC291503
0.8537	High Similarity	NPC261266
0.8533	High Similarity	NPC68443
0.8533	High Similarity	NPC201373
0.8519	High Similarity	NPC472265
0.8519	High Similarity	NPC221758
0.8519	High Similarity	NPC124172
0.8519	High Similarity	NPC209802
0.8519	High Similarity	NPC59453
0.8519	High Similarity	NPC470077
0.8519	High Similarity	NPC185568
0.85	High Similarity	NPC87489
0.85	High Similarity	NPC218616
0.85	High Similarity	NPC470049
0.85	High Similarity	NPC296701
0.85	High Similarity	NPC248886
0.85	High Similarity	NPC30166
0.8493	Intermediate Similarity	NPC216460
0.8481	Intermediate Similarity	NPC102253
0.8481	Intermediate Similarity	NPC13554
0.8481	Intermediate Similarity	NPC236237
0.8481	Intermediate Similarity	NPC322313
0.8472	Intermediate Similarity	NPC476039
0.8472	Intermediate Similarity	NPC222366
0.8472	Intermediate Similarity	NPC286669
0.8472	Intermediate Similarity	NPC149680
0.8462	Intermediate Similarity	NPC83351
0.8462	Intermediate Similarity	NPC312328
0.8462	Intermediate Similarity	NPC167891
0.8442	Intermediate Similarity	NPC106364
0.8434	Intermediate Similarity	NPC58063
0.8434	Intermediate Similarity	NPC149224
0.8434	Intermediate Similarity	NPC271967
0.8421	Intermediate Similarity	NPC91858
0.8421	Intermediate Similarity	NPC100334
0.8415	Intermediate Similarity	NPC266511
0.8415	Intermediate Similarity	NPC474189
0.8415	Intermediate Similarity	NPC474349
0.8415	Intermediate Similarity	NPC318390
0.84	Intermediate Similarity	NPC111234
0.84	Intermediate Similarity	NPC110799
0.8395	Intermediate Similarity	NPC82538
0.8395	Intermediate Similarity	NPC477818
0.8395	Intermediate Similarity	NPC237795
0.8354	Intermediate Similarity	NPC472463
0.8333	Intermediate Similarity	NPC2158
0.8333	Intermediate Similarity	NPC91594
0.8313	Intermediate Similarity	NPC145879
0.8313	Intermediate Similarity	NPC477604
0.8313	Intermediate Similarity	NPC31564
0.8313	Intermediate Similarity	NPC155011
0.8313	Intermediate Similarity	NPC51014
0.8313	Intermediate Similarity	NPC24277
0.8313	Intermediate Similarity	NPC474733
0.8313	Intermediate Similarity	NPC152808
0.8313	Intermediate Similarity	NPC474732
0.8313	Intermediate Similarity	NPC6391
0.8313	Intermediate Similarity	NPC293287
0.8313	Intermediate Similarity	NPC474970
0.8313	Intermediate Similarity	NPC94462
0.8313	Intermediate Similarity	NPC474778
0.8312	Intermediate Similarity	NPC477923
0.8312	Intermediate Similarity	NPC103822

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 NPC76931 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1281
0.2-0.3	4267
0.3-0.4	2384
0.4-0.5	598
0.5-0.6	190
0.6-0.7	166
0.7-0.8	59
0.8-0.85	15
0.85-0.9	8
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9583	High Similarity	NPD7339	Approved
0.9583	High Similarity	NPD6942	Approved
0.9167	High Similarity	NPD7151	Approved
0.9167	High Similarity	NPD7150	Approved
0.9167	High Similarity	NPD7152	Approved
0.9028	High Similarity	NPD7143	Approved
0.9028	High Similarity	NPD7144	Approved
0.8933	High Similarity	NPD3701	Clinical (unspecified phase)
0.8919	High Similarity	NPD6926	Approved
0.8919	High Similarity	NPD6924	Approved
0.8889	High Similarity	NPD6922	Approved
0.8889	High Similarity	NPD6923	Approved
0.8684	High Similarity	NPD6933	Approved
0.8667	High Similarity	NPD4784	Approved
0.8667	High Similarity	NPD4785	Approved
0.8519	High Similarity	NPD4786	Approved
0.8481	Intermediate Similarity	NPD7525	Registered
0.84	Intermediate Similarity	NPD4243	Approved
0.8354	Intermediate Similarity	NPD6929	Approved
0.8333	Intermediate Similarity	NPD6932	Approved
0.8272	Intermediate Similarity	NPD3667	Approved
0.825	Intermediate Similarity	NPD6931	Approved
0.825	Intermediate Similarity	NPD6930	Phase 2
0.8228	Intermediate Similarity	NPD7145	Approved
0.8101	Intermediate Similarity	NPD5776	Phase 2
0.8101	Intermediate Similarity	NPD6925	Approved
0.8025	Intermediate Similarity	NPD7514	Phase 3
0.8025	Intermediate Similarity	NPD7509	Discontinued
0.8	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6695	Phase 3
0.7927	Intermediate Similarity	NPD6902	Approved
0.7901	Intermediate Similarity	NPD7645	Phase 2
0.7901	Intermediate Similarity	NPD6683	Phase 2
0.7857	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4190	Phase 3
0.7848	Intermediate Similarity	NPD5275	Approved
0.7848	Intermediate Similarity	NPD8264	Approved
0.7841	Intermediate Similarity	NPD6079	Approved
0.7816	Intermediate Similarity	NPD5328	Approved
0.7805	Intermediate Similarity	NPD7332	Phase 2
0.7805	Intermediate Similarity	NPD4748	Discontinued
0.7765	Intermediate Similarity	NPD6893	Approved
0.7683	Intermediate Similarity	NPD4195	Approved
0.7674	Intermediate Similarity	NPD3618	Phase 1
0.7674	Intermediate Similarity	NPD5279	Phase 3
0.7647	Intermediate Similarity	NPD3133	Approved
0.7647	Intermediate Similarity	NPD3665	Phase 1
0.7647	Intermediate Similarity	NPD3666	Approved
0.7586	Intermediate Similarity	NPD7750	Discontinued
0.7586	Intermediate Similarity	NPD7524	Approved
0.7556	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD6898	Phase 1
0.7442	Intermediate Similarity	NPD3668	Phase 3
0.7363	Intermediate Similarity	NPD4202	Approved
0.7312	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5221	Approved
0.7312	Intermediate Similarity	NPD5222	Approved
0.7253	Intermediate Similarity	NPD7087	Discontinued
0.7234	Intermediate Similarity	NPD5173	Approved
0.7222	Intermediate Similarity	NPD4753	Phase 2
0.7209	Intermediate Similarity	NPD4221	Approved
0.7209	Intermediate Similarity	NPD4223	Phase 3
0.7159	Intermediate Similarity	NPD5329	Approved
0.7159	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4697	Phase 3
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7079	Intermediate Similarity	NPD5280	Approved
0.7079	Intermediate Similarity	NPD4694	Approved
0.7065	Intermediate Similarity	NPD7637	Suspended
0.7053	Intermediate Similarity	NPD4755	Approved
0.7045	Intermediate Similarity	NPD4197	Approved
0.7021	Intermediate Similarity	NPD5210	Approved
0.7021	Intermediate Similarity	NPD4629	Approved
0.701	Intermediate Similarity	NPD5223	Approved
0.6979	Remote Similarity	NPD5290	Discontinued
0.6957	Remote Similarity	NPD7136	Phase 2
0.6939	Remote Similarity	NPD5226	Approved
0.6939	Remote Similarity	NPD4633	Approved
0.6939	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD5211	Phase 2
0.6939	Remote Similarity	NPD5225	Approved
0.6932	Remote Similarity	NPD4788	Approved
0.6907	Remote Similarity	NPD4700	Approved
0.6889	Remote Similarity	NPD6684	Approved
0.6889	Remote Similarity	NPD4693	Phase 3
0.6889	Remote Similarity	NPD7521	Approved
0.6889	Remote Similarity	NPD5330	Approved
0.6889	Remote Similarity	NPD4689	Approved
0.6889	Remote Similarity	NPD7146	Approved
0.6889	Remote Similarity	NPD5690	Phase 2
0.6889	Remote Similarity	NPD4688	Approved
0.6889	Remote Similarity	NPD6409	Approved
0.6889	Remote Similarity	NPD4138	Approved
0.6889	Remote Similarity	NPD7334	Approved
0.6889	Remote Similarity	NPD5205	Approved
0.6889	Remote Similarity	NPD4690	Approved
0.6882	Remote Similarity	NPD7515	Phase 2
0.6882	Remote Similarity	NPD5281	Approved
0.6882	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD6084	Phase 2
0.6875	Remote Similarity	NPD6083	Phase 2
0.6869	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD5174	Approved
0.6848	Remote Similarity	NPD6051	Approved
0.6804	Remote Similarity	NPD7638	Approved
0.68	Remote Similarity	NPD5141	Approved
0.679	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6881	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6744	Remote Similarity	NPD3617	Approved
0.6739	Remote Similarity	NPD5737	Approved
0.6739	Remote Similarity	NPD4518	Approved
0.6739	Remote Similarity	NPD6903	Approved
0.6739	Remote Similarity	NPD4722	Approved
0.6739	Remote Similarity	NPD4723	Approved
0.6739	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6672	Approved
0.6735	Remote Similarity	NPD7639	Approved
0.6735	Remote Similarity	NPD7640	Approved
0.6733	Remote Similarity	NPD6675	Approved
0.6733	Remote Similarity	NPD7128	Approved
0.6733	Remote Similarity	NPD6402	Approved
0.6733	Remote Similarity	NPD5739	Approved
0.6707	Remote Similarity	NPD4787	Phase 1
0.6702	Remote Similarity	NPD6411	Approved
0.67	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD4058	Approved
0.6635	Remote Similarity	NPD6883	Approved
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6627	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7320	Approved
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD4730	Approved
0.6602	Remote Similarity	NPD4729	Approved
0.6596	Remote Similarity	NPD4096	Approved
0.6596	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4695	Discontinued
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD6847	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6617	Approved
0.6569	Remote Similarity	NPD4768	Approved
0.6569	Remote Similarity	NPD4767	Approved
0.6562	Remote Similarity	NPD7748	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6373	Approved
0.6538	Remote Similarity	NPD6372	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6533	Remote Similarity	NPD4219	Approved
0.6526	Remote Similarity	NPD8035	Phase 2
0.6526	Remote Similarity	NPD8034	Phase 2
0.6522	Remote Similarity	NPD6098	Approved
0.6522	Remote Similarity	NPD4519	Discontinued
0.6522	Remote Similarity	NPD4623	Approved
0.6522	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4692	Approved
0.6517	Remote Similarity	NPD4139	Approved
0.6509	Remote Similarity	NPD6882	Approved
0.6509	Remote Similarity	NPD8297	Approved
0.6506	Remote Similarity	NPD4747	Approved
0.6505	Remote Similarity	NPD5701	Approved
0.6495	Remote Similarity	NPD5695	Phase 3
0.6489	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5250	Approved
0.6476	Remote Similarity	NPD5248	Approved
0.6476	Remote Similarity	NPD5251	Approved
0.6476	Remote Similarity	NPD4634	Approved
0.6476	Remote Similarity	NPD5249	Phase 3
0.6476	Remote Similarity	NPD5169	Approved
0.6476	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5247	Approved
0.6476	Remote Similarity	NPD5135	Approved
0.6471	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5696	Approved
0.6463	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5133	Approved
0.6442	Remote Similarity	NPD5128	Approved
0.6429	Remote Similarity	NPD5276	Approved
0.6422	Remote Similarity	NPD7115	Discovery
0.6421	Remote Similarity	NPD5207	Approved
0.6415	Remote Similarity	NPD5216	Approved
0.6415	Remote Similarity	NPD5215	Approved
0.6415	Remote Similarity	NPD5127	Approved
0.6415	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5217	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