NPASS Compound

Structure

CID16701 OpenBabel06191715342D 33 38 0 0 1 0 0 0 0 0999 V2000 -4.4513 -1.0861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0802 3.7967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5160 2.3897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7149 2.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6517 2.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6242 4.6869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8110 3.2809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8124 4.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6231 2.8120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4366 3.2807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8126 1.4057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7149 1.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5351 -0.8911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2465 1.8737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4363 4.2180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0006 2.8123 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0006 1.8746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6248 2.8123 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6248 1.8746 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1201 1.8737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4353 1.4054 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4347 0.4686 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6231 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8127 3.2812 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6232 1.8742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8116 1.4057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9080 -1.5870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3087 4.7218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4972 1.3709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0569 1.8737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6517 1.0625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2459 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 20 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 31 1 0 0 0 0 13 27 2 0 0 0 0 13 32 1 0 0 0 0 14 21 1 0 0 0 0 15 28 1 6 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 26 1 1 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 19 29 1 1 0 0 0 20 30 2 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 6 0 0 0 22 23 1 0 0 0 0 22 32 1 6 0 0 0 23 26 1 1 0 0 0 23 33 1 0 0 0 0 24 2 1 6 0 0 0 25 26 1 6 0 0 0 26 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.23
Volume:	457.899
LogP:	2.785
LogD:	3.18
LogS:	-3.922
# Rotatable Bonds:	3
TPSA:	109.5
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	5.393
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.058
MDCK Permeability:	5.499715553014539e-05
Pgp-inhibitor:	0.057
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.718
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.314
Plasma Protein Binding (PPB):	79.64109802246094%
Volume Distribution (VD):	1.38
Pgp-substrate:	16.425758361816406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.395
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.381
CYP2C9-inhibitor:	0.141
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.405

ADMET: Excretion

Clearance (CL):	8.023
Half-life (T1/2):	0.643

ADMET: Toxicity

hERG Blockers:	0.837
Human Hepatotoxicity (H-HT):	0.924
Drug-inuced Liver Injury (DILI):	0.639
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.589
Skin Sensitization:	0.29
Carcinogencity:	0.256
Eye Corrosion:	0.099
Eye Irritation:	0.031
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC16701

Natural Product ID:	NPC16701
*Common Name:**	KWAUEUQHUYWWTO-CBFFWNJESA-N
IUPAC Name:	n.a.
Synonyms:	6Alpha-Hydroxycinobufagin
Standard InCHIKey:	KWAUEUQHUYWWTO-CBFFWNJESA-N
Standard InCHI:	InChI=1S/C26H34O7/c1-13(27)32-22-21(14-4-5-20(30)31-12-14)25(3)9-7-16-17(26(25)23(22)33-26)11-19(29)18-10-15(28)6-8-24(16,18)2/h4-5,12,15-19,21-23,28-29H,6-11H2,1-3H3/t15-,16-,17+,18-,19-,21-,22+,23+,24+,25+,26+/m0/s1
SMILES:	O[C@H]1CC[C@]2([C@@H](C1)[C@@H](O)C[C@@H]1[C@@H]2CC[C@]2([C@]31O[C@@H]3[C@@H]([C@@H]2c1ccc(=O)oc1)OC(=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515220
PubChem CID:	10939450
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides 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
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575946]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141860]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	venom	n.a.	n.a.	PMID[24050254]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28256122]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	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	9

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.87	ug.mL-1	PMID[548131]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.038	ug.mL-1	PMID[548131]
NPT1366	Cell Line	MH60	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[548131]
NPT1081	Cell Line	BXPC-3	Homo sapiens	IC50	=	0.46	ug.mL-1	PMID[548131]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.36	ug.mL-1	PMID[548131]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	0.32	ug.mL-1	PMID[548131]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	0.74	ug.mL-1	PMID[548131]
NPT575	Cell Line	KM-20L2	Homo sapiens	IC50	=	0.28	ug.mL-1	PMID[548131]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	0.21	ug.mL-1	PMID[548131]

☑ 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 NPC16701 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	387
0.1-0.2	1429
0.2-0.3	2893
0.3-0.4	5362
0.4-0.5	10345
0.5-0.6	10084
0.6-0.7	9801
0.7-0.8	2041
0.8-0.85	272
0.85-0.9	35
0.9-0.95	28
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC213761
0.9908	High Similarity	NPC35171
0.9908	High Similarity	NPC278681
0.9907	High Similarity	NPC157380
0.9818	High Similarity	NPC112936
0.9725	High Similarity	NPC185287
0.945	High Similarity	NPC171126
0.9381	High Similarity	NPC312481
0.9358	High Similarity	NPC44537
0.9352	High Similarity	NPC103491
0.9259	High Similarity	NPC75389
0.9217	High Similarity	NPC6193
0.9167	High Similarity	NPC275060
0.9074	High Similarity	NPC79298
0.9074	High Similarity	NPC43063
0.9	High Similarity	NPC12795
0.8991	High Similarity	NPC304276
0.8991	High Similarity	NPC137462
0.8898	High Similarity	NPC159499
0.8807	High Similarity	NPC295843
0.8796	High Similarity	NPC171014
0.8761	High Similarity	NPC241977
0.8636	High Similarity	NPC220217
0.8636	High Similarity	NPC119855
0.8632	High Similarity	NPC145074
0.8632	High Similarity	NPC114939
0.8632	High Similarity	NPC41123
0.8632	High Similarity	NPC257610
0.8609	High Similarity	NPC232564
0.8609	High Similarity	NPC113425
0.8596	High Similarity	NPC154815
0.8584	High Similarity	NPC470076
0.8584	High Similarity	NPC183603
0.8545	High Similarity	NPC165969
0.8509	High Similarity	NPC247760
0.8403	Intermediate Similarity	NPC233500
0.839	Intermediate Similarity	NPC219656
0.839	Intermediate Similarity	NPC153085
0.839	Intermediate Similarity	NPC268326
0.8376	Intermediate Similarity	NPC290693
0.8374	Intermediate Similarity	NPC221414
0.8362	Intermediate Similarity	NPC216665
0.8333	Intermediate Similarity	NPC16270
0.8333	Intermediate Similarity	NPC196130
0.8333	Intermediate Similarity	NPC115349
0.8319	Intermediate Similarity	NPC79579
0.8305	Intermediate Similarity	NPC146786
0.8304	Intermediate Similarity	NPC469960
0.8304	Intermediate Similarity	NPC29389
0.8304	Intermediate Similarity	NPC93026
0.8304	Intermediate Similarity	NPC186668
0.8304	Intermediate Similarity	NPC265502
0.8291	Intermediate Similarity	NPC470075
0.8288	Intermediate Similarity	NPC97487
0.8288	Intermediate Similarity	NPC196471
0.8288	Intermediate Similarity	NPC187302
0.8288	Intermediate Similarity	NPC10232
0.8288	Intermediate Similarity	NPC160583
0.8288	Intermediate Similarity	NPC472821
0.8288	Intermediate Similarity	NPC189588
0.8279	Intermediate Similarity	NPC179261
0.8273	Intermediate Similarity	NPC268829
0.8273	Intermediate Similarity	NPC222875
0.8273	Intermediate Similarity	NPC247701
0.8273	Intermediate Similarity	NPC25177
0.8273	Intermediate Similarity	NPC295110
0.8264	Intermediate Similarity	NPC55602
0.8264	Intermediate Similarity	NPC219804
0.8261	Intermediate Similarity	NPC71680
0.825	Intermediate Similarity	NPC67569
0.8241	Intermediate Similarity	NPC299654
0.8235	Intermediate Similarity	NPC305260
0.8235	Intermediate Similarity	NPC44899
0.8235	Intermediate Similarity	NPC29639
0.8235	Intermediate Similarity	NPC304260
0.8235	Intermediate Similarity	NPC5883
0.8235	Intermediate Similarity	NPC270850
0.823	Intermediate Similarity	NPC472263
0.823	Intermediate Similarity	NPC108682
0.823	Intermediate Similarity	NPC469959
0.823	Intermediate Similarity	NPC469957
0.8214	Intermediate Similarity	NPC472822
0.8205	Intermediate Similarity	NPC69576
0.8205	Intermediate Similarity	NPC471633
0.8205	Intermediate Similarity	NPC31354
0.8205	Intermediate Similarity	NPC43213
0.8205	Intermediate Similarity	NPC84949
0.8198	Intermediate Similarity	NPC470972
0.8197	Intermediate Similarity	NPC8374
0.819	Intermediate Similarity	NPC214005
0.819	Intermediate Similarity	NPC150228
0.8182	Intermediate Similarity	NPC471082
0.8182	Intermediate Similarity	NPC470265
0.8182	Intermediate Similarity	NPC23786
0.8174	Intermediate Similarity	NPC15551
0.8167	Intermediate Similarity	NPC474370
0.8167	Intermediate Similarity	NPC184555
0.8151	Intermediate Similarity	NPC153440
0.8142	Intermediate Similarity	NPC471206
0.8142	Intermediate Similarity	NPC470980
0.814	Intermediate Similarity	NPC75616
0.8136	Intermediate Similarity	NPC193382
0.8136	Intermediate Similarity	NPC99620
0.8136	Intermediate Similarity	NPC5311
0.8136	Intermediate Similarity	NPC298278
0.8136	Intermediate Similarity	NPC310341
0.8136	Intermediate Similarity	NPC199428
0.8125	Intermediate Similarity	NPC297617
0.812	Intermediate Similarity	NPC73050
0.8115	Intermediate Similarity	NPC469789
0.8108	Intermediate Similarity	NPC475617
0.8103	Intermediate Similarity	NPC471484
0.8103	Intermediate Similarity	NPC284162
0.8103	Intermediate Similarity	NPC255401
0.8103	Intermediate Similarity	NPC262083
0.8099	Intermediate Similarity	NPC475219
0.8099	Intermediate Similarity	NPC231518
0.8091	Intermediate Similarity	NPC278673
0.8087	Intermediate Similarity	NPC475030
0.8083	Intermediate Similarity	NPC264954
0.8083	Intermediate Similarity	NPC5292
0.807	Intermediate Similarity	NPC472820
0.8067	Intermediate Similarity	NPC309034
0.8067	Intermediate Similarity	NPC142066
0.8067	Intermediate Similarity	NPC244402
0.8067	Intermediate Similarity	NPC87250
0.8067	Intermediate Similarity	NPC473852
0.8067	Intermediate Similarity	NPC158344
0.8067	Intermediate Similarity	NPC243196
0.8067	Intermediate Similarity	NPC471354
0.8067	Intermediate Similarity	NPC203862
0.8067	Intermediate Similarity	NPC471351
0.8067	Intermediate Similarity	NPC474418
0.8067	Intermediate Similarity	NPC196429
0.8067	Intermediate Similarity	NPC77319
0.8067	Intermediate Similarity	NPC34390
0.8067	Intermediate Similarity	NPC471355
0.8067	Intermediate Similarity	NPC157376
0.8067	Intermediate Similarity	NPC99728
0.8067	Intermediate Similarity	NPC27507
0.8067	Intermediate Similarity	NPC84987
0.8067	Intermediate Similarity	NPC50305
0.8067	Intermediate Similarity	NPC471353
0.8067	Intermediate Similarity	NPC93883
0.8067	Intermediate Similarity	NPC152615
0.8053	Intermediate Similarity	NPC200861
0.8053	Intermediate Similarity	NPC473543
0.8051	Intermediate Similarity	NPC265290
0.8051	Intermediate Similarity	NPC305044
0.8047	Intermediate Similarity	NPC158350
0.8036	Intermediate Similarity	NPC475344
0.8036	Intermediate Similarity	NPC476471
0.8034	Intermediate Similarity	NPC241477
0.8033	Intermediate Similarity	NPC107493
0.8033	Intermediate Similarity	NPC193893
0.8033	Intermediate Similarity	NPC88326
0.8033	Intermediate Similarity	NPC153700
0.8018	Intermediate Similarity	NPC13743
0.8018	Intermediate Similarity	NPC79631
0.8018	Intermediate Similarity	NPC98813
0.8017	Intermediate Similarity	NPC177047
0.8017	Intermediate Similarity	NPC238850
0.8017	Intermediate Similarity	NPC474585
0.8	Intermediate Similarity	NPC83287
0.8	Intermediate Similarity	NPC50774
0.8	Intermediate Similarity	NPC472080
0.8	Intermediate Similarity	NPC50124
0.8	Intermediate Similarity	NPC709
0.7984	Intermediate Similarity	NPC62172
0.7984	Intermediate Similarity	NPC293112
0.7984	Intermediate Similarity	NPC289700
0.7983	Intermediate Similarity	NPC190286
0.7982	Intermediate Similarity	NPC266570
0.7982	Intermediate Similarity	NPC189863
0.7982	Intermediate Similarity	NPC472818
0.7967	Intermediate Similarity	NPC11895
0.7966	Intermediate Similarity	NPC101965
0.7966	Intermediate Similarity	NPC101400
0.7965	Intermediate Similarity	NPC45897
0.7965	Intermediate Similarity	NPC474124
0.7965	Intermediate Similarity	NPC473523
0.7953	Intermediate Similarity	NPC155529
0.7951	Intermediate Similarity	NPC40749
0.7951	Intermediate Similarity	NPC46570
0.7946	Intermediate Similarity	NPC155974
0.7934	Intermediate Similarity	NPC291820
0.7934	Intermediate Similarity	NPC469756
0.7934	Intermediate Similarity	NPC329905
0.7934	Intermediate Similarity	NPC32177
0.7934	Intermediate Similarity	NPC236973
0.7934	Intermediate Similarity	NPC292467
0.7934	Intermediate Similarity	NPC30483
0.7934	Intermediate Similarity	NPC81222
0.7934	Intermediate Similarity	NPC475041
0.7934	Intermediate Similarity	NPC470897
0.7934	Intermediate Similarity	NPC55532
0.7928	Intermediate Similarity	NPC218107
0.7928	Intermediate Similarity	NPC65700
0.792	Intermediate Similarity	NPC287423
0.7917	Intermediate Similarity	NPC470492

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 NPC16701 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	870
0.2-0.3	1735
0.3-0.4	2649
0.4-0.5	2170
0.5-0.6	1020
0.6-0.7	339
0.7-0.8	30
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8559	High Similarity	NPD7503	Approved
0.8099	Intermediate Similarity	NPD8033	Approved
0.8	Intermediate Similarity	NPD7327	Approved
0.8	Intermediate Similarity	NPD7328	Approved
0.7934	Intermediate Similarity	NPD7516	Approved
0.7928	Intermediate Similarity	NPD7638	Approved
0.7917	Intermediate Similarity	NPD7115	Discovery
0.7869	Intermediate Similarity	NPD8377	Approved
0.7869	Intermediate Similarity	NPD8294	Approved
0.7857	Intermediate Similarity	NPD7640	Approved
0.7857	Intermediate Similarity	NPD7639	Approved
0.7805	Intermediate Similarity	NPD8335	Approved
0.7805	Intermediate Similarity	NPD8380	Approved
0.7805	Intermediate Similarity	NPD8378	Approved
0.7805	Intermediate Similarity	NPD8379	Approved
0.7805	Intermediate Similarity	NPD8296	Approved
0.7559	Intermediate Similarity	NPD7507	Approved
0.7544	Intermediate Similarity	NPD6648	Approved
0.7478	Intermediate Similarity	NPD5344	Discontinued
0.7438	Intermediate Similarity	NPD6053	Discontinued
0.7385	Intermediate Similarity	NPD7319	Approved
0.7308	Intermediate Similarity	NPD7736	Approved
0.7302	Intermediate Similarity	NPD6319	Approved
0.7295	Intermediate Similarity	NPD8297	Approved
0.7265	Intermediate Similarity	NPD7632	Discontinued
0.725	Intermediate Similarity	NPD6881	Approved
0.725	Intermediate Similarity	NPD6899	Approved
0.7236	Intermediate Similarity	NPD4632	Approved
0.7209	Intermediate Similarity	NPD7492	Approved
0.719	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5697	Approved
0.7165	Intermediate Similarity	NPD6054	Approved
0.7155	Intermediate Similarity	NPD4225	Approved
0.7154	Intermediate Similarity	NPD6616	Approved
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7132	Intermediate Similarity	NPD7604	Phase 2
0.7131	Intermediate Similarity	NPD6883	Approved
0.7131	Intermediate Similarity	NPD7102	Approved
0.7131	Intermediate Similarity	NPD7290	Approved
0.7099	Intermediate Similarity	NPD7078	Approved
0.7083	Intermediate Similarity	NPD6402	Approved
0.7083	Intermediate Similarity	NPD6008	Approved
0.7083	Intermediate Similarity	NPD5739	Approved
0.7083	Intermediate Similarity	NPD7128	Approved
0.7083	Intermediate Similarity	NPD6675	Approved
0.7073	Intermediate Similarity	NPD8130	Phase 1
0.7073	Intermediate Similarity	NPD6650	Approved
0.7073	Intermediate Similarity	NPD6869	Approved
0.7073	Intermediate Similarity	NPD6649	Approved
0.7073	Intermediate Similarity	NPD6847	Approved
0.7073	Intermediate Similarity	NPD6617	Approved
0.7063	Intermediate Similarity	NPD6009	Approved
0.7054	Intermediate Similarity	NPD6370	Approved
0.7049	Intermediate Similarity	NPD6014	Approved
0.7049	Intermediate Similarity	NPD6013	Approved
0.7049	Intermediate Similarity	NPD6012	Approved
0.7016	Intermediate Similarity	NPD6882	Approved
0.6992	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6016	Approved
0.6977	Remote Similarity	NPD5983	Phase 2
0.6977	Remote Similarity	NPD6015	Approved
0.6967	Remote Similarity	NPD6011	Approved
0.6967	Remote Similarity	NPD6686	Approved
0.6967	Remote Similarity	NPD7320	Approved
0.693	Remote Similarity	NPD7637	Suspended
0.6923	Remote Similarity	NPD5988	Approved
0.6911	Remote Similarity	NPD6373	Approved
0.6911	Remote Similarity	NPD6372	Approved
0.6909	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6051	Approved
0.6899	Remote Similarity	NPD6059	Approved
0.6894	Remote Similarity	NPD6336	Discontinued
0.6885	Remote Similarity	NPD5701	Approved
0.6885	Remote Similarity	NPD6412	Phase 2
0.6875	Remote Similarity	NPD7524	Approved
0.6855	Remote Similarity	NPD4634	Approved
0.6852	Remote Similarity	NPD7525	Registered
0.6842	Remote Similarity	NPD8293	Discontinued
0.6833	Remote Similarity	NPD5211	Phase 2
0.6825	Remote Similarity	NPD8133	Approved
0.6818	Remote Similarity	NPD6695	Phase 3
0.6807	Remote Similarity	NPD5286	Approved
0.6807	Remote Similarity	NPD4696	Approved
0.6807	Remote Similarity	NPD5285	Approved
0.678	Remote Similarity	NPD6084	Phase 2
0.678	Remote Similarity	NPD6083	Phase 2
0.675	Remote Similarity	NPD4159	Approved
0.6748	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5141	Approved
0.672	Remote Similarity	NPD6371	Approved
0.6694	Remote Similarity	NPD5225	Approved
0.6694	Remote Similarity	NPD5224	Approved
0.6694	Remote Similarity	NPD5226	Approved
0.6694	Remote Similarity	NPD4633	Approved
0.6692	Remote Similarity	NPD7100	Approved
0.6692	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5174	Approved
0.6639	Remote Similarity	NPD4755	Approved
0.6639	Remote Similarity	NPD5175	Approved
0.6615	Remote Similarity	NPD6335	Approved
0.6612	Remote Similarity	NPD5223	Approved
0.6589	Remote Similarity	NPD6274	Approved
0.6583	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4202	Approved
0.6581	Remote Similarity	NPD6399	Phase 3
0.6579	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4250	Approved
0.6579	Remote Similarity	NPD7750	Discontinued
0.6579	Remote Similarity	NPD4251	Approved
0.6552	Remote Similarity	NPD6698	Approved
0.6552	Remote Similarity	NPD46	Approved
0.6545	Remote Similarity	NPD6931	Approved
0.6545	Remote Similarity	NPD6930	Phase 2
0.6545	Remote Similarity	NPD7514	Phase 3
0.6538	Remote Similarity	NPD6317	Approved
0.6529	Remote Similarity	NPD4700	Approved
0.6525	Remote Similarity	NPD7748	Approved
0.6522	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7260	Phase 2
0.65	Remote Similarity	NPD7902	Approved
0.6496	Remote Similarity	NPD5284	Approved
0.6496	Remote Similarity	NPD6079	Approved
0.6496	Remote Similarity	NPD5281	Approved
0.6496	Remote Similarity	NPD8034	Phase 2
0.6496	Remote Similarity	NPD7515	Phase 2
0.6496	Remote Similarity	NPD8035	Phase 2
0.6491	Remote Similarity	NPD4249	Approved
0.6489	Remote Similarity	NPD6313	Approved
0.6489	Remote Similarity	NPD6314	Approved
0.6486	Remote Similarity	NPD7236	Approved
0.6486	Remote Similarity	NPD6902	Approved
0.6471	Remote Similarity	NPD5695	Phase 3
0.6471	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8513	Phase 3
0.6463	Remote Similarity	NPD7625	Phase 1
0.6455	Remote Similarity	NPD6929	Approved
0.6455	Remote Similarity	NPD4195	Approved
0.6446	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD4729	Approved
0.6429	Remote Similarity	NPD4730	Approved
0.6429	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6033	Approved
0.6422	Remote Similarity	NPD6932	Approved
0.6404	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7332	Phase 2
0.637	Remote Similarity	NPD6067	Discontinued
0.6364	Remote Similarity	NPD7145	Approved
0.6356	Remote Similarity	NPD5693	Phase 1
0.6356	Remote Similarity	NPD7087	Discontinued
0.6349	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7146	Approved
0.6348	Remote Similarity	NPD6684	Approved
0.6348	Remote Similarity	NPD7334	Approved
0.6348	Remote Similarity	NPD5330	Approved
0.6348	Remote Similarity	NPD6409	Approved
0.6348	Remote Similarity	NPD7521	Approved
0.6343	Remote Similarity	NPD6909	Approved
0.6343	Remote Similarity	NPD8517	Approved
0.6343	Remote Similarity	NPD8515	Approved
0.6343	Remote Similarity	NPD6908	Approved
0.6343	Remote Similarity	NPD8516	Approved
0.6343	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4629	Approved
0.6333	Remote Similarity	NPD5210	Approved
0.633	Remote Similarity	NPD6933	Approved
0.633	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5247	Approved
0.6328	Remote Similarity	NPD5248	Approved
0.6328	Remote Similarity	NPD5250	Approved
0.6328	Remote Similarity	NPD5251	Approved
0.6328	Remote Similarity	NPD5249	Phase 3
0.6325	Remote Similarity	NPD4753	Phase 2
0.6325	Remote Similarity	NPD5328	Approved
0.6306	Remote Similarity	NPD7645	Phase 2
0.6299	Remote Similarity	NPD5128	Approved
0.6296	Remote Similarity	NPD6926	Approved
0.6296	Remote Similarity	NPD6924	Approved
0.6281	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5222	Approved
0.6281	Remote Similarity	NPD5221	Approved
0.6279	Remote Similarity	NPD5215	Approved
0.6279	Remote Similarity	NPD5217	Approved
0.6279	Remote Similarity	NPD5216	Approved
0.6275	Remote Similarity	NPD7239	Suspended
0.6273	Remote Similarity	NPD5776	Phase 2
0.6273	Remote Similarity	NPD6925	Approved
0.6271	Remote Similarity	NPD5785	Approved
0.627	Remote Similarity	NPD4767	Approved
0.627	Remote Similarity	NPD4768	Approved
0.6261	Remote Similarity	NPD6893	Approved
0.6258	Remote Similarity	NPD7799	Discontinued
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4819	Approved
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD8328	Phase 3

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