NPASS Compound

Structure

NPC472757 OpenBabel07101719252D 34 37 0 0 1 0 0 0 0 0999 V2000 1.7917 -3.9736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0449 -2.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2521 1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 -0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5753 -1.5387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7767 -2.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4921 0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4412 3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7541 2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0938 4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9033 -2.4868 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3011 1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 -0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7019 -2.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4452 3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9921 2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8584 -0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8884 -1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 0.9740 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 -0.1073 4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6870 -3.0256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5799 3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3265 1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 -1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 -0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 25 1 0 0 0 0 7 25 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 17 1 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 28 1 0 0 0 0 13 24 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 15 26 1 1 0 0 0 16 29 2 0 0 0 0 16 33 1 0 0 0 0 18 10 1 6 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 26 1 6 0 0 0 20 22 1 0 0 0 0 20 26 1 1 0 0 0 21 30 2 0 0 0 0 22 25 1 0 0 0 0 22 27 1 6 0 0 0 23 27 1 6 0 0 0 23 33 1 0 0 0 0 24 31 2 0 0 0 0 24 34 1 0 0 0 0 25 27 1 0 0 0 0 26 32 1 1 0 0 0 27 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.26
Volume:	489.672
LogP:	3.418
LogD:	2.282
LogS:	-4.322
# Rotatable Bonds:	7
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	5.217
Fsp3:	0.741
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.853
MDCK Permeability:	3.305858263047412e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.225

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.538
Plasma Protein Binding (PPB):	62.321746826171875%
Volume Distribution (VD):	1.033
Pgp-substrate:	43.51593780517578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.576
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.608
CYP3A4-substrate:	0.304

ADMET: Excretion

Clearance (CL):	4.329
Half-life (T1/2):	0.709

ADMET: Toxicity

hERG Blockers:	0.736
Human Hepatotoxicity (H-HT):	0.981
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.756
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.272
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC472757

Natural Product ID:	NPC472757
*Common Name:**	VLQRBYYAEZBEJX-IXSMXENYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VLQRBYYAEZBEJX-IXSMXENYSA-N
Standard InCHI:	InChI=1S/C27H38O7/c1-8-13(2)24(31)34-27-22(25(27,6)7)20-11-17(12-28)10-18-19(9-14(3)21(18)30)26(20,32)15(4)23(27)33-16(5)29/h9,11,13,15,18-20,22-23,28,32H,8,10,12H2,1-7H3/t13?,15-,18-,19-,20+,22-,23-,26+,27-/m1/s1
SMILES:	OCC1=C[C@H]2[C@@H]3C([C@]3(OC(=O)C(CC)C)[C@@H]([C@H]([C@@]2([C@H]2[C@@H](C1)C(=O)C(=C2)C)O)C)OC(=O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582004
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	Leaves	Langevin, La Reunion, France	2009-Nov	PMID[25946116]

☑ 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	3
Others	7

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Inhibition	<	40.0	%	PMID[523734]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	<	40.0	%	PMID[523734]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	<	40.0	%	PMID[523734]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	105000.0	nM	PMID[523734]
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	85000.0	nM	PMID[523734]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	13000.0	nM	PMID[523734]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	4.0	n.a.	PMID[523734]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	77000.0	nM	PMID[523734]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	1.4	n.a.	PMID[523734]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	85000.0	nM	PMID[523734]

☑ 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 NPC472757 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	234
0.1-0.2	1390
0.2-0.3	4334
0.3-0.4	7098
0.4-0.5	13898
0.5-0.6	7836
0.6-0.7	6248
0.7-0.8	1497
0.8-0.85	48
0.85-0.9	32
0.9-0.95	47
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
0.9905	High Similarity	NPC472400
0.9811	High Similarity	NPC471127
0.9811	High Similarity	NPC234858
0.9811	High Similarity	NPC154363
0.972	High Similarity	NPC10721
0.963	High Similarity	NPC472758
0.963	High Similarity	NPC472397
0.963	High Similarity	NPC171905
0.963	High Similarity	NPC471125
0.9541	High Similarity	NPC156745
0.9541	High Similarity	NPC5991
0.9541	High Similarity	NPC255081
0.9541	High Similarity	NPC5989
0.9541	High Similarity	NPC275696
0.9541	High Similarity	NPC471108
0.9541	High Similarity	NPC22628
0.9541	High Similarity	NPC236918
0.9537	High Similarity	NPC156252
0.9455	High Similarity	NPC472759
0.9455	High Similarity	NPC475885
0.9455	High Similarity	NPC157252
0.9455	High Similarity	NPC145182
0.9455	High Similarity	NPC471126
0.9455	High Similarity	NPC471128
0.9455	High Similarity	NPC329080
0.945	High Similarity	NPC124676
0.945	High Similarity	NPC146280
0.9369	High Similarity	NPC52839
0.9369	High Similarity	NPC472401
0.9286	High Similarity	NPC19464
0.9252	High Similarity	NPC475937
0.9252	High Similarity	NPC158523
0.9204	High Similarity	NPC472399
0.9159	High Similarity	NPC153036
0.9123	High Similarity	NPC145238
0.9115	High Similarity	NPC257017
0.9115	High Similarity	NPC162009
0.9083	High Similarity	NPC71889
0.9	High Similarity	NPC474872
0.8899	High Similarity	NPC96739
0.8899	High Similarity	NPC260786
0.8899	High Similarity	NPC474871
0.8899	High Similarity	NPC174471
0.8889	High Similarity	NPC163004
0.8839	High Similarity	NPC153651
0.8818	High Similarity	NPC151216
0.8818	High Similarity	NPC265499
0.8818	High Similarity	NPC17138
0.8818	High Similarity	NPC221511
0.8818	High Similarity	NPC475391
0.8818	High Similarity	NPC215643
0.8818	High Similarity	NPC89227
0.8818	High Similarity	NPC170212
0.8818	High Similarity	NPC101825
0.8772	High Similarity	NPC19336
0.8772	High Similarity	NPC185876
0.8761	High Similarity	NPC472760
0.8739	High Similarity	NPC474937
0.8739	High Similarity	NPC477091
0.8729	High Similarity	NPC270109
0.8684	High Similarity	NPC180640
0.8667	High Similarity	NPC189393
0.8667	High Similarity	NPC90814
0.8595	High Similarity	NPC476111
0.8559	High Similarity	NPC222307
0.8545	High Similarity	NPC273433
0.8522	High Similarity	NPC472667
0.8482	Intermediate Similarity	NPC472002
0.8475	Intermediate Similarity	NPC473919
0.8475	Intermediate Similarity	NPC473709
0.8421	Intermediate Similarity	NPC179626
0.839	Intermediate Similarity	NPC473802
0.8387	Intermediate Similarity	NPC243902
0.8364	Intermediate Similarity	NPC187435
0.8364	Intermediate Similarity	NPC67321
0.8333	Intermediate Similarity	NPC471940
0.8318	Intermediate Similarity	NPC470074
0.8291	Intermediate Similarity	NPC143755
0.8264	Intermediate Similarity	NPC236999
0.825	Intermediate Similarity	NPC293112
0.825	Intermediate Similarity	NPC471939
0.823	Intermediate Similarity	NPC469655
0.823	Intermediate Similarity	NPC474846
0.823	Intermediate Similarity	NPC469656
0.822	Intermediate Similarity	NPC310511
0.8198	Intermediate Similarity	NPC143609
0.819	Intermediate Similarity	NPC469684
0.8165	Intermediate Similarity	NPC476081
0.8158	Intermediate Similarity	NPC234042
0.8158	Intermediate Similarity	NPC152117
0.8151	Intermediate Similarity	NPC222688
0.8142	Intermediate Similarity	NPC253906
0.8142	Intermediate Similarity	NPC257240
0.8125	Intermediate Similarity	NPC306265
0.812	Intermediate Similarity	NPC251310
0.8115	Intermediate Similarity	NPC470850
0.8108	Intermediate Similarity	NPC111952
0.8103	Intermediate Similarity	NPC470793
0.8103	Intermediate Similarity	NPC471816
0.8091	Intermediate Similarity	NPC478057
0.8087	Intermediate Similarity	NPC962
0.8087	Intermediate Similarity	NPC250109
0.8087	Intermediate Similarity	NPC317210
0.8083	Intermediate Similarity	NPC469789
0.8083	Intermediate Similarity	NPC11895
0.8073	Intermediate Similarity	NPC97435
0.807	Intermediate Similarity	NPC188738
0.8067	Intermediate Similarity	NPC67569
0.8051	Intermediate Similarity	NPC469380
0.8051	Intermediate Similarity	NPC475041
0.8049	Intermediate Similarity	NPC104382
0.8049	Intermediate Similarity	NPC470851
0.8036	Intermediate Similarity	NPC230541
0.8034	Intermediate Similarity	NPC475323
0.8034	Intermediate Similarity	NPC473656
0.8017	Intermediate Similarity	NPC117712
0.8017	Intermediate Similarity	NPC81736
0.8017	Intermediate Similarity	NPC473798
0.8017	Intermediate Similarity	NPC172154
0.8	Intermediate Similarity	NPC162973
0.8	Intermediate Similarity	NPC136289
0.8	Intermediate Similarity	NPC170538
0.8	Intermediate Similarity	NPC23786
0.8	Intermediate Similarity	NPC269530
0.8	Intermediate Similarity	NPC137430
0.8	Intermediate Similarity	NPC474516
0.8	Intermediate Similarity	NPC470265
0.8	Intermediate Similarity	NPC470063
0.7983	Intermediate Similarity	NPC154491
0.7983	Intermediate Similarity	NPC4548
0.7983	Intermediate Similarity	NPC268530
0.7982	Intermediate Similarity	NPC5103
0.7982	Intermediate Similarity	NPC306856
0.7982	Intermediate Similarity	NPC477103
0.7982	Intermediate Similarity	NPC474718
0.7982	Intermediate Similarity	NPC476274
0.7982	Intermediate Similarity	NPC47024
0.7965	Intermediate Similarity	NPC472218
0.7965	Intermediate Similarity	NPC472219
0.7965	Intermediate Similarity	NPC472217
0.7965	Intermediate Similarity	NPC472439
0.7965	Intermediate Similarity	NPC469916
0.7965	Intermediate Similarity	NPC102843
0.7963	Intermediate Similarity	NPC111348
0.7951	Intermediate Similarity	NPC473635
0.7949	Intermediate Similarity	NPC474734
0.7949	Intermediate Similarity	NPC176840
0.7949	Intermediate Similarity	NPC40632
0.7949	Intermediate Similarity	NPC49492
0.7949	Intermediate Similarity	NPC266728
0.7949	Intermediate Similarity	NPC96312
0.7949	Intermediate Similarity	NPC251236
0.7949	Intermediate Similarity	NPC328374
0.7946	Intermediate Similarity	NPC102352
0.7946	Intermediate Similarity	NPC60315
0.7946	Intermediate Similarity	NPC323834
0.7934	Intermediate Similarity	NPC469352
0.7934	Intermediate Similarity	NPC473979
0.7931	Intermediate Similarity	NPC25909
0.7931	Intermediate Similarity	NPC474271
0.7931	Intermediate Similarity	NPC469454
0.7931	Intermediate Similarity	NPC46269
0.7931	Intermediate Similarity	NPC469463
0.7931	Intermediate Similarity	NPC106395
0.7931	Intermediate Similarity	NPC469496
0.7931	Intermediate Similarity	NPC49451
0.7931	Intermediate Similarity	NPC477126
0.7931	Intermediate Similarity	NPC471204
0.7928	Intermediate Similarity	NPC475623
0.7928	Intermediate Similarity	NPC473694
0.7928	Intermediate Similarity	NPC475334
0.7928	Intermediate Similarity	NPC61442
0.7928	Intermediate Similarity	NPC120321
0.7928	Intermediate Similarity	NPC99266
0.7928	Intermediate Similarity	NPC8196
0.792	Intermediate Similarity	NPC475139
0.792	Intermediate Similarity	NPC180902
0.7917	Intermediate Similarity	NPC4021
0.7917	Intermediate Similarity	NPC159456
0.7913	Intermediate Similarity	NPC317107
0.7913	Intermediate Similarity	NPC474229
0.7913	Intermediate Similarity	NPC470076
0.7909	Intermediate Similarity	NPC471412
0.7909	Intermediate Similarity	NPC476240
0.7909	Intermediate Similarity	NPC224720
0.7909	Intermediate Similarity	NPC115862
0.7909	Intermediate Similarity	NPC476223
0.7909	Intermediate Similarity	NPC81530
0.7903	Intermediate Similarity	NPC231529
0.7903	Intermediate Similarity	NPC175186
0.7899	Intermediate Similarity	NPC470186
0.7899	Intermediate Similarity	NPC312536
0.7895	Intermediate Similarity	NPC477102
0.7895	Intermediate Similarity	NPC141350
0.7895	Intermediate Similarity	NPC475586
0.7895	Intermediate Similarity	NPC469370
0.789	Intermediate Similarity	NPC216478
0.7881	Intermediate Similarity	NPC473968
0.7881	Intermediate Similarity	NPC58662
0.7881	Intermediate Similarity	NPC98249

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 NPC472757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1827
0.2-0.3	3664
0.3-0.4	2224
0.4-0.5	796
0.5-0.6	250
0.6-0.7	175
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8142	Intermediate Similarity	NPD6371	Approved
0.7748	Intermediate Similarity	NPD5344	Discontinued
0.7739	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD7115	Discovery
0.7672	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6648	Approved
0.7414	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD4225	Approved
0.7395	Intermediate Similarity	NPD8297	Approved
0.736	Intermediate Similarity	NPD7604	Phase 2
0.735	Intermediate Similarity	NPD6899	Approved
0.735	Intermediate Similarity	NPD6881	Approved
0.735	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7640	Approved
0.7345	Intermediate Similarity	NPD7639	Approved
0.7333	Intermediate Similarity	NPD4632	Approved
0.7328	Intermediate Similarity	NPD6402	Approved
0.7328	Intermediate Similarity	NPD5739	Approved
0.7328	Intermediate Similarity	NPD7128	Approved
0.7328	Intermediate Similarity	NPD6008	Approved
0.7328	Intermediate Similarity	NPD6675	Approved
0.7311	Intermediate Similarity	NPD6650	Approved
0.7311	Intermediate Similarity	NPD6649	Approved
0.7288	Intermediate Similarity	NPD6372	Approved
0.7288	Intermediate Similarity	NPD6373	Approved
0.7265	Intermediate Similarity	NPD5697	Approved
0.7258	Intermediate Similarity	NPD6319	Approved
0.7257	Intermediate Similarity	NPD7638	Approved
0.7227	Intermediate Similarity	NPD6883	Approved
0.7227	Intermediate Similarity	NPD7102	Approved
0.7227	Intermediate Similarity	NPD7290	Approved
0.7203	Intermediate Similarity	NPD6686	Approved
0.7203	Intermediate Similarity	NPD7320	Approved
0.7167	Intermediate Similarity	NPD6847	Approved
0.7167	Intermediate Similarity	NPD8130	Phase 1
0.7167	Intermediate Similarity	NPD6869	Approved
0.7167	Intermediate Similarity	NPD6617	Approved
0.7165	Intermediate Similarity	NPD7492	Approved
0.7154	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.712	Intermediate Similarity	NPD6054	Approved
0.7119	Intermediate Similarity	NPD5701	Approved
0.7117	Intermediate Similarity	NPD6399	Phase 3
0.7109	Intermediate Similarity	NPD6616	Approved
0.7109	Intermediate Similarity	NPD7507	Approved
0.7107	Intermediate Similarity	NPD6882	Approved
0.7091	Intermediate Similarity	NPD46	Approved
0.7091	Intermediate Similarity	NPD6698	Approved
0.7077	Intermediate Similarity	NPD7319	Approved
0.7069	Intermediate Similarity	NPD5211	Phase 2
0.7063	Intermediate Similarity	NPD5983	Phase 2
0.7059	Intermediate Similarity	NPD6011	Approved
0.7054	Intermediate Similarity	NPD7078	Approved
0.704	Intermediate Similarity	NPD7516	Approved
0.7018	Intermediate Similarity	NPD7902	Approved
0.7008	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD7736	Approved
0.6991	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6059	Approved
0.6977	Remote Similarity	NPD6336	Discontinued
0.6975	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6053	Discontinued
0.696	Remote Similarity	NPD7328	Approved
0.696	Remote Similarity	NPD7327	Approved
0.6949	Remote Similarity	NPD5141	Approved
0.6929	Remote Similarity	NPD6016	Approved
0.6929	Remote Similarity	NPD6015	Approved
0.6923	Remote Similarity	NPD8293	Discontinued
0.6903	Remote Similarity	NPD7748	Approved
0.6897	Remote Similarity	NPD5286	Approved
0.6897	Remote Similarity	NPD5285	Approved
0.6897	Remote Similarity	NPD4696	Approved
0.6885	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6079	Approved
0.6875	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD7515	Phase 2
0.687	Remote Similarity	NPD4755	Approved
0.687	Remote Similarity	NPD6083	Phase 2
0.687	Remote Similarity	NPD6084	Phase 2
0.686	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5328	Approved
0.6842	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6412	Phase 2
0.6822	Remote Similarity	NPD8328	Phase 3
0.6814	Remote Similarity	NPD5778	Approved
0.6814	Remote Similarity	NPD5779	Approved
0.6803	Remote Similarity	NPD4634	Approved
0.68	Remote Similarity	NPD6274	Approved
0.6789	Remote Similarity	NPD1696	Phase 3
0.678	Remote Similarity	NPD5224	Approved
0.678	Remote Similarity	NPD5226	Approved
0.678	Remote Similarity	NPD4633	Approved
0.678	Remote Similarity	NPD5225	Approved
0.678	Remote Similarity	NPD7632	Discontinued
0.6772	Remote Similarity	NPD7101	Approved
0.6772	Remote Similarity	NPD7100	Approved
0.6754	Remote Similarity	NPD5282	Discontinued
0.6754	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7900	Approved
0.6752	Remote Similarity	NPD4700	Approved
0.6727	Remote Similarity	NPD3618	Phase 1
0.6726	Remote Similarity	NPD7983	Approved
0.6726	Remote Similarity	NPD7637	Suspended
0.6723	Remote Similarity	NPD5174	Approved
0.6723	Remote Similarity	NPD5175	Approved
0.6696	Remote Similarity	NPD5695	Phase 3
0.6696	Remote Similarity	NPD1695	Approved
0.6695	Remote Similarity	NPD5223	Approved
0.6693	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6638	Remote Similarity	NPD5221	Approved
0.6638	Remote Similarity	NPD5222	Approved
0.6638	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4697	Phase 3
0.6637	Remote Similarity	NPD5785	Approved
0.6637	Remote Similarity	NPD7838	Discovery
0.6636	Remote Similarity	NPD1694	Approved
0.6614	Remote Similarity	NPD6317	Approved
0.6589	Remote Similarity	NPD8294	Approved
0.6589	Remote Similarity	NPD8377	Approved
0.6581	Remote Similarity	NPD5173	Approved
0.6579	Remote Similarity	NPD8034	Phase 2
0.6579	Remote Similarity	NPD8035	Phase 2
0.6562	Remote Similarity	NPD6313	Approved
0.6562	Remote Similarity	NPD6314	Approved
0.6545	Remote Similarity	NPD4786	Approved
0.6545	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7503	Approved
0.6538	Remote Similarity	NPD8516	Approved
0.6538	Remote Similarity	NPD8513	Phase 3
0.6538	Remote Similarity	NPD8517	Approved
0.6538	Remote Similarity	NPD6909	Approved
0.6538	Remote Similarity	NPD8515	Approved
0.6538	Remote Similarity	NPD6908	Approved
0.6538	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6868	Approved
0.6525	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD3573	Approved
0.6514	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8133	Approved
0.6504	Remote Similarity	NPD4729	Approved
0.6504	Remote Similarity	NPD4730	Approved
0.6504	Remote Similarity	NPD5128	Approved
0.6493	Remote Similarity	NPD6033	Approved
0.6486	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5363	Approved
0.6484	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4767	Approved
0.6475	Remote Similarity	NPD4768	Approved
0.6471	Remote Similarity	NPD7260	Phase 2
0.6466	Remote Similarity	NPD6001	Approved
0.646	Remote Similarity	NPD5737	Approved
0.646	Remote Similarity	NPD6672	Approved
0.6455	Remote Similarity	NPD6695	Phase 3
0.6455	Remote Similarity	NPD5362	Discontinued
0.6455	Remote Similarity	NPD7154	Phase 3
0.6449	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4754	Approved
0.6435	Remote Similarity	NPD5281	Approved
0.6435	Remote Similarity	NPD5284	Approved
0.6435	Remote Similarity	NPD6411	Approved
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6417	Remote Similarity	NPD1700	Approved
0.641	Remote Similarity	NPD5210	Approved
0.641	Remote Similarity	NPD4629	Approved
0.6404	Remote Similarity	NPD4753	Phase 2
0.64	Remote Similarity	NPD5251	Approved
0.64	Remote Similarity	NPD5247	Approved
0.64	Remote Similarity	NPD5250	Approved
0.64	Remote Similarity	NPD5249	Phase 3
0.64	Remote Similarity	NPD5248	Approved
0.6364	Remote Similarity	NPD3667	Approved
0.6349	Remote Similarity	NPD5216	Approved
0.6349	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5217	Approved
0.6349	Remote Similarity	NPD5215	Approved
0.6348	Remote Similarity	NPD3168	Discontinued
0.6339	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6067	Discontinued
0.6316	Remote Similarity	NPD6903	Approved
0.6306	Remote Similarity	NPD6110	Phase 1
0.6296	Remote Similarity	NPD8074	Phase 3
0.6283	Remote Similarity	NPD3574	Clinical (unspecified phase)

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