NPASS Compound

Structure

CID5292 OpenBabel06191715322D 38 42 0 0 1 0 0 0 0 0999 V2000 -4.0922 1.7825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6835 -0.0392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0298 2.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3211 -0.9223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1996 1.8943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9810 -2.8738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1515 -3.3534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9807 -1.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4916 -3.3538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6613 -2.8748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4908 -0.4786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6604 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8286 -1.4376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8289 -0.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5146 1.2704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8301 0.4790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4512 1.0710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7469 0.1602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8050 1.8217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3217 -2.8743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4911 -1.4366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6610 -1.9162 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1509 -1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8736 0.5589 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1059 -0.5513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3214 -1.9157 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9576 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8304 -0.4791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8306 -1.4371 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 2.6801 2.2116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1506 -0.4495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4016 -1.4622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7112 1.5986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8309 -2.4143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8464 0.4883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7052 0.8689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1692 -0.3520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 20 1 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 28 1 0 0 0 0 13 14 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 16 37 1 0 0 0 0 17 18 2 0 0 0 0 18 25 1 0 0 0 0 19 31 2 0 0 0 0 19 37 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 6 0 0 0 22 29 1 1 0 0 0 23 26 1 0 0 0 0 23 32 2 0 0 0 0 24 27 1 6 0 0 0 24 38 1 0 0 0 0 25 33 2 0 0 0 0 25 38 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 1 0 0 0 27 30 1 0 0 0 0 27 34 1 0 0 0 0 28 29 1 6 0 0 0 29 35 1 1 0 0 0 30 28 1 6 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.27
Volume:	539.157
LogP:	2.144
LogD:	0.962
LogS:	-4.292
# Rotatable Bonds:	5
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	5.75
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.043
MDCK Permeability:	1.1831531082862057e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.612
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	64.74462127685547%
Volume Distribution (VD):	0.75
Pgp-substrate:	25.966909408569336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.734
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.531
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.801
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	2.445
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.188
Human Hepatotoxicity (H-HT):	0.522
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.529
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.126
Carcinogencity:	0.858
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.825

Download Data

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

Natural Product: NPC5292

Natural Product ID:	NPC5292
*Common Name:**	RGHQRULWHKEQHE-GRVQADPTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RGHQRULWHKEQHE-GRVQADPTSA-N
Standard InCHI:	InChI=1S/C30H40O8/c1-17-15-24(38-25(33)18(17)2)27(5,34)30(36)14-13-29(35)22-10-9-20-7-6-8-23(32)26(20,4)21(22)11-12-28(29,30)16-37-19(3)31/h6,8-9,21-22,24,34-36H,7,10-16H2,1-5H3/t21-,22+,24+,26-,27-,28+,29+,30+/m0/s1
SMILES:	CC(=O)OC[C@]12CC[C@H]3[C@H]([C@]1(O)CC[C@@]2(O)[C@]([C@H]1CC(=C(C(=O)O1)C)C)(O)C)CC=C1[C@]3(C)C(=O)C=CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3605564
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO13447	Physalis chenopodifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13447	Physalis chenopodifolia	Species	Solanaceae	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
IC50	10
Others	2

Activity Type	# Activity
Cell Line	8
Individual Protein	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	IC50	=	580.0	nM	PMID[450540]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	IC50	=	750.0	nM	PMID[450540]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	IC50	=	770.0	nM	PMID[450540]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	70.0	nM	PMID[450540]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	130.0	nM	PMID[450540]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1900.0	nM	PMID[450540]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	1200.0	nM	PMID[450540]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	3400.0	nM	PMID[450540]
NPT859	Cell Line	HFF	Homo sapiens	IC50	>	3100.0	nM	PMID[450540]
NPT306	Cell Line	PC-3	Homo sapiens	TGI	=	66.0	%	PMID[450540]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	=	564.0	nM	PMID[450541]
NPT32	Organism	Mus musculus	Mus musculus	MTD	=	50.0	mg kg-1	PMID[450540]

☑ 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 NPC5292 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	236
0.1-0.2	1271
0.2-0.3	3979
0.3-0.4	7104
0.4-0.5	13135
0.5-0.6	6913
0.6-0.7	7029
0.7-0.8	2769
0.8-0.85	198
0.85-0.9	41
0.9-0.95	9
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC153440
0.973	High Similarity	NPC474585
0.973	High Similarity	NPC79579
0.9725	High Similarity	NPC190286
0.964	High Similarity	NPC270850
0.964	High Similarity	NPC305260
0.9558	High Similarity	NPC107493
0.9469	High Similarity	NPC46570
0.9369	High Similarity	NPC176840
0.8974	High Similarity	NPC473979
0.8957	High Similarity	NPC475041
0.8929	High Similarity	NPC236217
0.8919	High Similarity	NPC473627
0.8889	High Similarity	NPC269642
0.8824	High Similarity	NPC473635
0.8814	High Similarity	NPC469789
0.8772	High Similarity	NPC474181
0.8761	High Similarity	NPC191620
0.876	High Similarity	NPC231529
0.875	High Similarity	NPC37116
0.8729	High Similarity	NPC23786
0.8729	High Similarity	NPC170538
0.8729	High Similarity	NPC470265
0.8689	High Similarity	NPC173347
0.8678	High Similarity	NPC245094
0.8667	High Similarity	NPC293112
0.8655	High Similarity	NPC11895
0.8644	High Similarity	NPC310511
0.8644	High Similarity	NPC67569
0.8618	High Similarity	NPC471855
0.8595	High Similarity	NPC287423
0.8584	High Similarity	NPC197428
0.8583	High Similarity	NPC8369
0.8583	High Similarity	NPC172154
0.8583	High Similarity	NPC81736
0.8583	High Similarity	NPC8374
0.856	High Similarity	NPC158350
0.8559	High Similarity	NPC474370
0.8547	High Similarity	NPC257457
0.8547	High Similarity	NPC311554
0.8537	High Similarity	NPC213634
0.8534	High Similarity	NPC148458
0.8525	High Similarity	NPC311534
0.8522	High Similarity	NPC25909
0.8522	High Similarity	NPC194100
0.8522	High Similarity	NPC962
0.8522	High Similarity	NPC471204
0.8522	High Similarity	NPC250109
0.8509	High Similarity	NPC470961
0.85	High Similarity	NPC204812
0.85	High Similarity	NPC6193
0.8487	Intermediate Similarity	NPC202051
0.8475	Intermediate Similarity	NPC472667
0.8475	Intermediate Similarity	NPC475520
0.8475	Intermediate Similarity	NPC264954
0.8475	Intermediate Similarity	NPC473203
0.8468	Intermediate Similarity	NPC155529
0.8462	Intermediate Similarity	NPC239273
0.8455	Intermediate Similarity	NPC471407
0.8455	Intermediate Similarity	NPC475320
0.8455	Intermediate Similarity	NPC221414
0.8448	Intermediate Similarity	NPC470953
0.8443	Intermediate Similarity	NPC470882
0.8443	Intermediate Similarity	NPC473265
0.8435	Intermediate Similarity	NPC475524
0.8435	Intermediate Similarity	NPC221144
0.8435	Intermediate Similarity	NPC100267
0.843	Intermediate Similarity	NPC241456
0.843	Intermediate Similarity	NPC32868
0.8421	Intermediate Similarity	NPC29133
0.8417	Intermediate Similarity	NPC88326
0.8417	Intermediate Similarity	NPC153700
0.8407	Intermediate Similarity	NPC472825
0.8403	Intermediate Similarity	NPC476961
0.839	Intermediate Similarity	NPC475913
0.839	Intermediate Similarity	NPC186525
0.839	Intermediate Similarity	NPC709
0.839	Intermediate Similarity	NPC50774
0.8376	Intermediate Similarity	NPC64318
0.8376	Intermediate Similarity	NPC266728
0.8376	Intermediate Similarity	NPC49492
0.8361	Intermediate Similarity	NPC159499
0.8347	Intermediate Similarity	NPC120724
0.8347	Intermediate Similarity	NPC27363
0.8333	Intermediate Similarity	NPC472216
0.8333	Intermediate Similarity	NPC173905
0.8333	Intermediate Similarity	NPC5475
0.8333	Intermediate Similarity	NPC284828
0.8319	Intermediate Similarity	NPC476529
0.8319	Intermediate Similarity	NPC61520
0.8319	Intermediate Similarity	NPC475775
0.8319	Intermediate Similarity	NPC77689
0.8319	Intermediate Similarity	NPC144459
0.8319	Intermediate Similarity	NPC473636
0.8319	Intermediate Similarity	NPC474179
0.8319	Intermediate Similarity	NPC475834
0.8306	Intermediate Similarity	NPC476966
0.8306	Intermediate Similarity	NPC470880
0.8305	Intermediate Similarity	NPC134430
0.8305	Intermediate Similarity	NPC470492
0.8305	Intermediate Similarity	NPC471854
0.8305	Intermediate Similarity	NPC167606
0.8305	Intermediate Similarity	NPC286528
0.8305	Intermediate Similarity	NPC473968
0.8305	Intermediate Similarity	NPC20302
0.8305	Intermediate Similarity	NPC140055
0.8293	Intermediate Similarity	NPC473253
0.8291	Intermediate Similarity	NPC67259
0.8291	Intermediate Similarity	NPC326542
0.8291	Intermediate Similarity	NPC178289
0.8291	Intermediate Similarity	NPC147912
0.8288	Intermediate Similarity	NPC22388
0.8279	Intermediate Similarity	NPC473255
0.8279	Intermediate Similarity	NPC469790
0.8276	Intermediate Similarity	NPC152117
0.8276	Intermediate Similarity	NPC126691
0.8276	Intermediate Similarity	NPC269530
0.8276	Intermediate Similarity	NPC234042
0.8264	Intermediate Similarity	NPC222688
0.8261	Intermediate Similarity	NPC5103
0.8261	Intermediate Similarity	NPC41551
0.8261	Intermediate Similarity	NPC50223
0.825	Intermediate Similarity	NPC145074
0.825	Intermediate Similarity	NPC109607
0.825	Intermediate Similarity	NPC251226
0.825	Intermediate Similarity	NPC143755
0.825	Intermediate Similarity	NPC107338
0.825	Intermediate Similarity	NPC114939
0.825	Intermediate Similarity	NPC41123
0.8246	Intermediate Similarity	NPC65941
0.8235	Intermediate Similarity	NPC473720
0.8235	Intermediate Similarity	NPC288679
0.8235	Intermediate Similarity	NPC475372
0.8235	Intermediate Similarity	NPC329736
0.823	Intermediate Similarity	NPC323834
0.8226	Intermediate Similarity	NPC473620
0.8226	Intermediate Similarity	NPC473888
0.822	Intermediate Similarity	NPC476963
0.8217	Intermediate Similarity	NPC75616
0.8211	Intermediate Similarity	NPC250556
0.8211	Intermediate Similarity	NPC469750
0.8205	Intermediate Similarity	NPC317210
0.8205	Intermediate Similarity	NPC255017
0.8205	Intermediate Similarity	NPC469463
0.8205	Intermediate Similarity	NPC469454
0.8205	Intermediate Similarity	NPC469496
0.8203	Intermediate Similarity	NPC127656
0.8197	Intermediate Similarity	NPC55602
0.819	Intermediate Similarity	NPC304180
0.819	Intermediate Similarity	NPC470076
0.819	Intermediate Similarity	NPC179798
0.8182	Intermediate Similarity	NPC159456
0.8182	Intermediate Similarity	NPC312481
0.8182	Intermediate Similarity	NPC4021
0.8175	Intermediate Similarity	NPC231240
0.8174	Intermediate Similarity	NPC41405
0.8174	Intermediate Similarity	NPC304495
0.8167	Intermediate Similarity	NPC312536
0.8167	Intermediate Similarity	NPC476960
0.8167	Intermediate Similarity	NPC473839
0.8167	Intermediate Similarity	NPC278681
0.8167	Intermediate Similarity	NPC211093
0.816	Intermediate Similarity	NPC104382
0.816	Intermediate Similarity	NPC175186
0.816	Intermediate Similarity	NPC473593
0.8158	Intermediate Similarity	NPC475294
0.8158	Intermediate Similarity	NPC91034
0.8151	Intermediate Similarity	NPC470493
0.8151	Intermediate Similarity	NPC312824
0.8151	Intermediate Similarity	NPC55296
0.8151	Intermediate Similarity	NPC183580
0.8151	Intermediate Similarity	NPC476959
0.8151	Intermediate Similarity	NPC470959
0.8151	Intermediate Similarity	NPC475809
0.8151	Intermediate Similarity	NPC476965
0.8151	Intermediate Similarity	NPC284068
0.8145	Intermediate Similarity	NPC471356
0.8145	Intermediate Similarity	NPC152091
0.8145	Intermediate Similarity	NPC240070
0.8145	Intermediate Similarity	NPC117702
0.8145	Intermediate Similarity	NPC471357
0.8145	Intermediate Similarity	NPC469757
0.8145	Intermediate Similarity	NPC146456
0.8145	Intermediate Similarity	NPC179412
0.8145	Intermediate Similarity	NPC42399
0.8145	Intermediate Similarity	NPC329784
0.8136	Intermediate Similarity	NPC305044
0.8136	Intermediate Similarity	NPC43213
0.8136	Intermediate Similarity	NPC471398
0.8136	Intermediate Similarity	NPC473898
0.8136	Intermediate Similarity	NPC265290
0.8136	Intermediate Similarity	NPC216665
0.813	Intermediate Similarity	NPC470922
0.813	Intermediate Similarity	NPC318135
0.8125	Intermediate Similarity	NPC473928
0.8125	Intermediate Similarity	NPC473424
0.812	Intermediate Similarity	NPC280782
0.812	Intermediate Similarity	NPC470063
0.812	Intermediate Similarity	NPC277769
0.812	Intermediate Similarity	NPC207251

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 NPC5292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	1492
0.2-0.3	3651
0.3-0.4	2422
0.4-0.5	842
0.5-0.6	259
0.6-0.7	158
0.7-0.8	119
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8305	Intermediate Similarity	NPD7115	Discovery
0.8276	Intermediate Similarity	NPD8297	Approved
0.825	Intermediate Similarity	NPD6319	Approved
0.8211	Intermediate Similarity	NPD7507	Approved
0.8205	Intermediate Similarity	NPD4632	Approved
0.812	Intermediate Similarity	NPD6053	Discontinued
0.8087	Intermediate Similarity	NPD6881	Approved
0.8087	Intermediate Similarity	NPD6899	Approved
0.8034	Intermediate Similarity	NPD6649	Approved
0.8034	Intermediate Similarity	NPD6650	Approved
0.8033	Intermediate Similarity	NPD7503	Approved
0.8016	Intermediate Similarity	NPD7319	Approved
0.8	Intermediate Similarity	NPD5697	Approved
0.7966	Intermediate Similarity	NPD6882	Approved
0.7949	Intermediate Similarity	NPD7290	Approved
0.7949	Intermediate Similarity	NPD7102	Approved
0.7949	Intermediate Similarity	NPD6883	Approved
0.7913	Intermediate Similarity	NPD6675	Approved
0.7913	Intermediate Similarity	NPD7128	Approved
0.7913	Intermediate Similarity	NPD5739	Approved
0.7913	Intermediate Similarity	NPD6402	Approved
0.7881	Intermediate Similarity	NPD6617	Approved
0.7881	Intermediate Similarity	NPD6869	Approved
0.7881	Intermediate Similarity	NPD6847	Approved
0.7881	Intermediate Similarity	NPD8130	Phase 1
0.7863	Intermediate Similarity	NPD6372	Approved
0.7863	Intermediate Similarity	NPD6012	Approved
0.7863	Intermediate Similarity	NPD6014	Approved
0.7863	Intermediate Similarity	NPD6013	Approved
0.7863	Intermediate Similarity	NPD6373	Approved
0.7851	Intermediate Similarity	NPD6009	Approved
0.784	Intermediate Similarity	NPD7492	Approved
0.7805	Intermediate Similarity	NPD6054	Approved
0.7795	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD6616	Approved
0.7778	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD6011	Approved
0.776	Intermediate Similarity	NPD7604	Phase 2
0.7759	Intermediate Similarity	NPD6008	Approved
0.7742	Intermediate Similarity	NPD5983	Phase 2
0.7742	Intermediate Similarity	NPD8033	Approved
0.7717	Intermediate Similarity	NPD7078	Approved
0.7699	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD6412	Phase 2
0.7692	Intermediate Similarity	NPD5701	Approved
0.768	Intermediate Similarity	NPD6370	Approved
0.7652	Intermediate Similarity	NPD5211	Phase 2
0.7647	Intermediate Similarity	NPD4634	Approved
0.7642	Intermediate Similarity	NPD7327	Approved
0.7642	Intermediate Similarity	NPD7328	Approved
0.7638	Intermediate Similarity	NPD6336	Discontinued
0.7632	Intermediate Similarity	NPD7639	Approved
0.7632	Intermediate Similarity	NPD5286	Approved
0.7632	Intermediate Similarity	NPD7640	Approved
0.7632	Intermediate Similarity	NPD4696	Approved
0.7632	Intermediate Similarity	NPD5285	Approved
0.7627	Intermediate Similarity	NPD6686	Approved
0.76	Intermediate Similarity	NPD6016	Approved
0.76	Intermediate Similarity	NPD6015	Approved
0.7589	Intermediate Similarity	NPD5695	Phase 3
0.7581	Intermediate Similarity	NPD7516	Approved
0.754	Intermediate Similarity	NPD5988	Approved
0.7521	Intermediate Similarity	NPD5141	Approved
0.752	Intermediate Similarity	NPD6059	Approved
0.752	Intermediate Similarity	NPD8377	Approved
0.752	Intermediate Similarity	NPD8294	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.7481	Intermediate Similarity	NPD7260	Phase 2
0.746	Intermediate Similarity	NPD8380	Approved
0.746	Intermediate Similarity	NPD8378	Approved
0.746	Intermediate Similarity	NPD8379	Approved
0.746	Intermediate Similarity	NPD8335	Approved
0.746	Intermediate Similarity	NPD8296	Approved
0.7456	Intermediate Similarity	NPD6083	Phase 2
0.7456	Intermediate Similarity	NPD4755	Approved
0.7456	Intermediate Similarity	NPD6084	Phase 2
0.7442	Intermediate Similarity	NPD8293	Discontinued
0.744	Intermediate Similarity	NPD7101	Approved
0.744	Intermediate Similarity	NPD7100	Approved
0.7438	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5175	Approved
0.7436	Intermediate Similarity	NPD5174	Approved
0.7417	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5223	Approved
0.736	Intermediate Similarity	NPD6335	Approved
0.7355	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6371	Approved
0.7339	Intermediate Similarity	NPD6274	Approved
0.7333	Intermediate Similarity	NPD4729	Approved
0.7333	Intermediate Similarity	NPD4730	Approved
0.7328	Intermediate Similarity	NPD4700	Approved
0.7321	Intermediate Similarity	NPD5281	Approved
0.7321	Intermediate Similarity	NPD6079	Approved
0.7321	Intermediate Similarity	NPD5284	Approved
0.728	Intermediate Similarity	NPD6317	Approved
0.7257	Intermediate Similarity	NPD6399	Phase 3
0.725	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5696	Approved
0.7222	Intermediate Similarity	NPD6313	Approved
0.7222	Intermediate Similarity	NPD6314	Approved
0.7213	Intermediate Similarity	NPD5247	Approved
0.7213	Intermediate Similarity	NPD5249	Phase 3
0.7213	Intermediate Similarity	NPD5248	Approved
0.7213	Intermediate Similarity	NPD5251	Approved
0.7213	Intermediate Similarity	NPD5250	Approved
0.7207	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8513	Phase 3
0.7182	Intermediate Similarity	NPD6409	Approved
0.7182	Intermediate Similarity	NPD5330	Approved
0.7182	Intermediate Similarity	NPD7521	Approved
0.7182	Intermediate Similarity	NPD7334	Approved
0.7182	Intermediate Similarity	NPD6684	Approved
0.7182	Intermediate Similarity	NPD7146	Approved
0.7177	Intermediate Similarity	NPD8133	Approved
0.7168	Intermediate Similarity	NPD5693	Phase 1
0.7167	Intermediate Similarity	NPD4768	Approved
0.7167	Intermediate Similarity	NPD4767	Approved
0.7143	Intermediate Similarity	NPD5328	Approved
0.713	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4202	Approved
0.7094	Intermediate Similarity	NPD4225	Approved
0.708	Intermediate Similarity	NPD46	Approved
0.708	Intermediate Similarity	NPD6698	Approved
0.7077	Intermediate Similarity	NPD8328	Phase 3
0.7069	Intermediate Similarity	NPD5222	Approved
0.7069	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5221	Approved
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7054	Intermediate Similarity	NPD6903	Approved
0.7054	Intermediate Similarity	NPD6909	Approved
0.7054	Intermediate Similarity	NPD8517	Approved
0.7054	Intermediate Similarity	NPD8515	Approved
0.7054	Intermediate Similarity	NPD6908	Approved
0.7054	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD8516	Approved
0.7049	Intermediate Similarity	NPD5128	Approved
0.7043	Intermediate Similarity	NPD7748	Approved
0.7037	Intermediate Similarity	NPD6845	Suspended
0.7027	Intermediate Similarity	NPD5690	Phase 2
0.7018	Intermediate Similarity	NPD6050	Approved
0.7018	Intermediate Similarity	NPD5694	Approved
0.7016	Intermediate Similarity	NPD5217	Approved
0.7016	Intermediate Similarity	NPD5216	Approved
0.7016	Intermediate Similarity	NPD5215	Approved
0.7009	Intermediate Similarity	NPD7902	Approved
0.7009	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD4754	Approved
0.6992	Remote Similarity	NPD6033	Approved
0.6992	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4753	Phase 2
0.6991	Remote Similarity	NPD6080	Approved
0.6991	Remote Similarity	NPD6673	Approved
0.6991	Remote Similarity	NPD6904	Approved
0.6983	Remote Similarity	NPD5210	Approved
0.6983	Remote Similarity	NPD4629	Approved
0.6975	Remote Similarity	NPD5344	Discontinued
0.6964	Remote Similarity	NPD3573	Approved
0.6957	Remote Similarity	NPD5779	Approved
0.6957	Remote Similarity	NPD5778	Approved
0.6937	Remote Similarity	NPD1694	Approved
0.6935	Remote Similarity	NPD5169	Approved
0.6935	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5135	Approved
0.693	Remote Similarity	NPD5692	Phase 3
0.693	Remote Similarity	NPD5785	Approved
0.693	Remote Similarity	NPD5207	Approved
0.6929	Remote Similarity	NPD6868	Approved
0.6903	Remote Similarity	NPD5737	Approved
0.6903	Remote Similarity	NPD6672	Approved
0.688	Remote Similarity	NPD5127	Approved
0.688	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6411	Approved
0.687	Remote Similarity	NPD7515	Phase 2
0.6847	Remote Similarity	NPD3133	Approved
0.6847	Remote Similarity	NPD3666	Approved
0.6847	Remote Similarity	NPD3665	Phase 1
0.6842	Remote Similarity	NPD6051	Approved
0.6818	Remote Similarity	NPD4223	Phase 3
0.6818	Remote Similarity	NPD6435	Approved
0.6818	Remote Similarity	NPD4221	Approved
0.6786	Remote Similarity	NPD5329	Approved
0.6783	Remote Similarity	NPD7838	Discovery
0.6781	Remote Similarity	NPD7236	Approved
0.678	Remote Similarity	NPD4697	Phase 3
0.6754	Remote Similarity	NPD5208	Approved
0.6752	Remote Similarity	NPD6001	Approved
0.6752	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7900	Approved
0.675	Remote Similarity	NPD6648	Approved
0.6744	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3618	Phase 1
0.6726	Remote Similarity	NPD4694	Approved
0.6726	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6098	Approved
0.6726	Remote Similarity	NPD5280	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