NPASS Compound

Structure

NPC118638 OpenBabel07101718282D 42 47 0 0 1 0 0 0 0 0999 V2000 -4.8973 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9847 -4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2500 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9192 -5.1132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6102 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9921 -2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7709 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6757 -3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6320 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 -3.0032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5591 -6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7709 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3024 -3.3305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9629 -4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3448 -2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 2 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 31 1 0 0 0 0 9 10 2 0 0 0 0 9 22 1 0 0 0 0 10 33 1 0 0 0 0 11 12 1 0 0 0 0 11 31 1 0 0 0 0 13 23 1 0 0 0 0 13 32 1 0 0 0 0 14 16 1 0 0 0 0 14 35 1 0 0 0 0 15 33 1 0 0 0 0 15 34 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 17 26 1 0 0 0 0 18 3 1 6 0 0 0 18 22 1 0 0 0 0 18 25 1 0 0 0 0 19 4 1 1 0 0 0 19 24 1 0 0 0 0 19 27 1 0 0 0 0 20 36 2 0 0 0 0 20 40 1 0 0 0 0 21 37 2 0 0 0 0 21 41 1 0 0 0 0 22 38 2 0 0 0 0 23 24 1 0 0 0 0 23 40 1 1 0 0 0 24 31 1 1 0 0 0 25 28 1 0 0 0 0 25 33 1 1 0 0 0 26 39 2 0 0 0 0 27 26 1 1 0 0 0 27 41 1 0 0 0 0 28 29 1 0 0 0 0 28 42 1 1 0 0 0 29 30 1 0 0 0 0 29 42 1 1 0 0 0 30 32 1 6 0 0 0 30 34 1 0 0 0 0 31 32 1 1 0 0 0 32 8 1 6 0 0 0 33 34 1 6 0 0 0 34 12 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.32
Volume:	599.784
LogP:	3.547
LogD:	2.811
LogS:	-4.422
# Rotatable Bonds:	10
TPSA:	119.5
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.257
Synthetic Accessibility Score:	6.611
Fsp3:	0.765
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.442
MDCK Permeability:	4.43488170276396e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.51
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.455
Plasma Protein Binding (PPB):	79.82283782958984%
Volume Distribution (VD):	1.609
Pgp-substrate:	16.812660217285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.276
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.903
CYP3A4-substrate:	0.629

ADMET: Excretion

Clearance (CL):	2.205
Half-life (T1/2):	0.216

ADMET: Toxicity

hERG Blockers:	0.637
Human Hepatotoxicity (H-HT):	0.528
Drug-inuced Liver Injury (DILI):	0.645
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.482
Carcinogencity:	0.736
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC118638

Natural Product ID:	NPC118638
*Common Name:**	AXTVNDHMIGPHIQ-JGCPAILOSA-N
IUPAC Name:	n.a.
Synonyms:	6Beta,7Beta-Oxidoneoboutomellerone
Standard InCHIKey:	AXTVNDHMIGPHIQ-JGCPAILOSA-N
Standard InCHI:	InChI=1S/C34H46O8/c1-16(14-35)17(2)26(39)27(41-21(6)37)19(4)24-23(40-20(5)36)13-32(8)30-29-28(42-29)25-18(3)22(38)9-10-33(25)15-34(30,33)12-11-31(24,32)7/h9-10,16,18-19,23-25,27-30,35H,2,11-15H2,1,3-8H3/t16-,18+,19-,23-,24-,25+,27+,28-,29-,30-,31+,32-,33+,34-/m0/s1
SMILES:	OC[C@@H](C(=C)C(=O)[C@@H]([C@H]([C@H]1[C@@H](OC(=O)C)C[C@@]2([C@]1(C)CC[C@@]13[C@H]2[C@H]2O[C@H]2[C@@H]2[C@]3(C1)C=CC(=O)[C@H]2C)C)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1941159
PubChem CID:	57332229
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22168134]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22206869]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	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	2
Others	6

Activity Type	# Activity
Others	8

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	15.0	n.a.	PMID[468245]
NPT2	Others	Unspecified	FC	=	72.0	n.a.	PMID[468245]
NPT2	Others	Unspecified	FC	=	2.8	n.a.	PMID[468245]
NPT2	Others	Unspecified	IC50	=	60000.0	nM	PMID[468245]
NPT2	Others	Unspecified	IC50	=	48000.0	nM	PMID[468245]
NPT2	Others	Unspecified	FC	=	15.0	n.a.	PMID[468246]
NPT2	Others	Unspecified	FC	=	72.0	n.a.	PMID[468246]
NPT2	Others	Unspecified	FC	=	2.8	n.a.	PMID[468246]

☑ 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 NPC118638 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	248
0.1-0.2	1539
0.2-0.3	5276
0.3-0.4	9589
0.4-0.5	11611
0.5-0.6	6753
0.6-0.7	5657
0.7-0.8	1875
0.8-0.85	128
0.85-0.9	10
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9815	High Similarity	NPC270958
0.963	High Similarity	NPC202889
0.9537	High Similarity	NPC170487
0.9537	High Similarity	NPC71348
0.9444	High Similarity	NPC231589
0.9444	High Similarity	NPC118860
0.9444	High Similarity	NPC214797
0.9259	High Similarity	NPC241927
0.9259	High Similarity	NPC258543
0.9167	High Similarity	NPC470269
0.9	High Similarity	NPC197428
0.8981	High Similarity	NPC181265
0.8919	High Similarity	NPC470281
0.8889	High Similarity	NPC235889
0.8818	High Similarity	NPC94529
0.8727	High Similarity	NPC44063
0.8716	High Similarity	NPC29705
0.8716	High Similarity	NPC310586
0.8704	High Similarity	NPC271266
0.8704	High Similarity	NPC308351
0.8673	High Similarity	NPC280782
0.8649	High Similarity	NPC211224
0.8636	High Similarity	NPC475571
0.8636	High Similarity	NPC278628
0.8636	High Similarity	NPC196528
0.8636	High Similarity	NPC231530
0.8609	High Similarity	NPC148458
0.8596	High Similarity	NPC472926
0.8596	High Similarity	NPC52634
0.8571	High Similarity	NPC2766
0.8571	High Similarity	NPC304495
0.8547	High Similarity	NPC473203
0.8534	High Similarity	NPC471854
0.8534	High Similarity	NPC472927
0.8534	High Similarity	NPC239273
0.8532	High Similarity	NPC15396
0.8509	High Similarity	NPC100267
0.8509	High Similarity	NPC475524
0.8468	Intermediate Similarity	NPC470267
0.8462	Intermediate Similarity	NPC257457
0.8462	Intermediate Similarity	NPC311554
0.8455	Intermediate Similarity	NPC140723
0.8435	Intermediate Similarity	NPC962
0.843	Intermediate Similarity	NPC15095
0.8426	Intermediate Similarity	NPC114274
0.8421	Intermediate Similarity	NPC43775
0.839	Intermediate Similarity	NPC472933
0.8378	Intermediate Similarity	NPC96268
0.8374	Intermediate Similarity	NPC470880
0.8364	Intermediate Similarity	NPC22388
0.8361	Intermediate Similarity	NPC473253
0.8348	Intermediate Similarity	NPC264634
0.8347	Intermediate Similarity	NPC473255
0.8333	Intermediate Similarity	NPC222688
0.8333	Intermediate Similarity	NPC129689
0.8333	Intermediate Similarity	NPC108078
0.832	Intermediate Similarity	NPC58029
0.832	Intermediate Similarity	NPC469674
0.8319	Intermediate Similarity	NPC109973
0.8304	Intermediate Similarity	NPC470309
0.8304	Intermediate Similarity	NPC265127
0.8291	Intermediate Similarity	NPC298278
0.8291	Intermediate Similarity	NPC266728
0.8291	Intermediate Similarity	NPC49492
0.8288	Intermediate Similarity	NPC159442
0.8279	Intermediate Similarity	NPC63186
0.8276	Intermediate Similarity	NPC194100
0.8276	Intermediate Similarity	NPC250109
0.8261	Intermediate Similarity	NPC207689
0.8261	Intermediate Similarity	NPC115303
0.8257	Intermediate Similarity	NPC477854
0.825	Intermediate Similarity	NPC310511
0.8246	Intermediate Similarity	NPC286174
0.8246	Intermediate Similarity	NPC77947
0.824	Intermediate Similarity	NPC34963
0.824	Intermediate Similarity	NPC471855
0.8235	Intermediate Similarity	NPC476960
0.823	Intermediate Similarity	NPC475294
0.823	Intermediate Similarity	NPC3316
0.823	Intermediate Similarity	NPC144854
0.8226	Intermediate Similarity	NPC35109
0.8214	Intermediate Similarity	NPC135854
0.8214	Intermediate Similarity	NPC470251
0.8214	Intermediate Similarity	NPC137657
0.8214	Intermediate Similarity	NPC2436
0.8214	Intermediate Similarity	NPC216245
0.8211	Intermediate Similarity	NPC470882
0.8211	Intermediate Similarity	NPC473265
0.8205	Intermediate Similarity	NPC473798
0.8198	Intermediate Similarity	NPC136289
0.819	Intermediate Similarity	NPC147180
0.819	Intermediate Similarity	NPC221144
0.819	Intermediate Similarity	NPC152117
0.819	Intermediate Similarity	NPC234042
0.8182	Intermediate Similarity	NPC65858
0.8182	Intermediate Similarity	NPC472972
0.8182	Intermediate Similarity	NPC218383
0.8182	Intermediate Similarity	NPC144956
0.8182	Intermediate Similarity	NPC15390
0.8175	Intermediate Similarity	NPC469673
0.8174	Intermediate Similarity	NPC76084
0.8167	Intermediate Similarity	NPC241192
0.816	Intermediate Similarity	NPC220757
0.816	Intermediate Similarity	NPC241935
0.816	Intermediate Similarity	NPC279478
0.816	Intermediate Similarity	NPC196921
0.8158	Intermediate Similarity	NPC154608
0.8158	Intermediate Similarity	NPC192813
0.8158	Intermediate Similarity	NPC277017
0.8148	Intermediate Similarity	NPC469599
0.8142	Intermediate Similarity	NPC50535
0.8142	Intermediate Similarity	NPC96377
0.8136	Intermediate Similarity	NPC40632
0.8136	Intermediate Similarity	NPC251236
0.8136	Intermediate Similarity	NPC96312
0.8136	Intermediate Similarity	NPC328374
0.813	Intermediate Similarity	NPC473635
0.8125	Intermediate Similarity	NPC70967
0.8125	Intermediate Similarity	NPC470310
0.8125	Intermediate Similarity	NPC33973
0.8125	Intermediate Similarity	NPC275583
0.812	Intermediate Similarity	NPC317210
0.812	Intermediate Similarity	NPC472929
0.8115	Intermediate Similarity	NPC469789
0.8115	Intermediate Similarity	NPC267822
0.8115	Intermediate Similarity	NPC43252
0.8115	Intermediate Similarity	NPC204812
0.8115	Intermediate Similarity	NPC135038
0.8115	Intermediate Similarity	NPC120724
0.811	Intermediate Similarity	NPC476823
0.8108	Intermediate Similarity	NPC477356
0.8108	Intermediate Similarity	NPC224720
0.8108	Intermediate Similarity	NPC476240
0.8108	Intermediate Similarity	NPC81530
0.8108	Intermediate Similarity	NPC476223
0.8103	Intermediate Similarity	NPC472928
0.8083	Intermediate Similarity	NPC161065
0.8083	Intermediate Similarity	NPC61520
0.8083	Intermediate Similarity	NPC475041
0.808	Intermediate Similarity	NPC471407
0.808	Intermediate Similarity	NPC221414
0.8073	Intermediate Similarity	NPC477853
0.8073	Intermediate Similarity	NPC305483
0.8073	Intermediate Similarity	NPC200054
0.8073	Intermediate Similarity	NPC173272
0.8073	Intermediate Similarity	NPC328162
0.8073	Intermediate Similarity	NPC42042
0.8073	Intermediate Similarity	NPC96859
0.8073	Intermediate Similarity	NPC29410
0.807	Intermediate Similarity	NPC176949
0.807	Intermediate Similarity	NPC220974
0.807	Intermediate Similarity	NPC472925
0.807	Intermediate Similarity	NPC251824
0.807	Intermediate Similarity	NPC201908
0.807	Intermediate Similarity	NPC86852
0.8067	Intermediate Similarity	NPC153651
0.8067	Intermediate Similarity	NPC472934
0.8065	Intermediate Similarity	NPC305496
0.8065	Intermediate Similarity	NPC287423
0.8056	Intermediate Similarity	NPC196485
0.8056	Intermediate Similarity	NPC111015
0.8056	Intermediate Similarity	NPC245972
0.8053	Intermediate Similarity	NPC255309
0.8053	Intermediate Similarity	NPC47281
0.8053	Intermediate Similarity	NPC28656
0.8051	Intermediate Similarity	NPC474906
0.8051	Intermediate Similarity	NPC471398
0.8051	Intermediate Similarity	NPC18547
0.8049	Intermediate Similarity	NPC169818
0.8049	Intermediate Similarity	NPC32868
0.8049	Intermediate Similarity	NPC8374
0.8049	Intermediate Similarity	NPC241456
0.8036	Intermediate Similarity	NPC53222
0.8036	Intermediate Similarity	NPC477054
0.8033	Intermediate Similarity	NPC23786
0.8033	Intermediate Similarity	NPC470265
0.8033	Intermediate Similarity	NPC269642
0.8018	Intermediate Similarity	NPC112167
0.8018	Intermediate Similarity	NPC476274
0.8017	Intermediate Similarity	NPC321556
0.8017	Intermediate Similarity	NPC471406
0.8017	Intermediate Similarity	NPC185876
0.8017	Intermediate Similarity	NPC19336
0.8017	Intermediate Similarity	NPC5284
0.8017	Intermediate Similarity	NPC6206
0.8017	Intermediate Similarity	NPC163314
0.8	Intermediate Similarity	NPC275539
0.8	Intermediate Similarity	NPC21326
0.8	Intermediate Similarity	NPC189075
0.8	Intermediate Similarity	NPC329736
0.8	Intermediate Similarity	NPC470420
0.8	Intermediate Similarity	NPC295244
0.8	Intermediate Similarity	NPC18509
0.8	Intermediate Similarity	NPC469844
0.8	Intermediate Similarity	NPC293850
0.8	Intermediate Similarity	NPC236999
0.8	Intermediate Similarity	NPC190554
0.7984	Intermediate Similarity	NPC293112
0.7984	Intermediate Similarity	NPC47113
0.7984	Intermediate Similarity	NPC174367

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 NPC118638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	1770
0.2-0.3	3988
0.3-0.4	2104
0.4-0.5	594
0.5-0.6	222
0.6-0.7	121
0.7-0.8	102
0.8-0.85	30
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD6650	Approved
0.8919	High Similarity	NPD6649	Approved
0.8839	High Similarity	NPD8297	Approved
0.8818	High Similarity	NPD6899	Approved
0.8818	High Similarity	NPD6881	Approved
0.875	High Similarity	NPD8130	Phase 1
0.8739	High Similarity	NPD6373	Approved
0.8739	High Similarity	NPD6372	Approved
0.8727	High Similarity	NPD5697	Approved
0.8673	High Similarity	NPD6882	Approved
0.8661	High Similarity	NPD6883	Approved
0.8661	High Similarity	NPD7290	Approved
0.8661	High Similarity	NPD7102	Approved
0.8649	High Similarity	NPD6011	Approved
0.8636	High Similarity	NPD7128	Approved
0.8636	High Similarity	NPD6675	Approved
0.8636	High Similarity	NPD6402	Approved
0.8636	High Similarity	NPD5739	Approved
0.8584	High Similarity	NPD6617	Approved
0.8584	High Similarity	NPD6847	Approved
0.8584	High Similarity	NPD6869	Approved
0.8571	High Similarity	NPD6014	Approved
0.8571	High Similarity	NPD6013	Approved
0.8571	High Similarity	NPD6012	Approved
0.8571	High Similarity	NPD7604	Phase 2
0.8482	Intermediate Similarity	NPD7320	Approved
0.8475	Intermediate Similarity	NPD6319	Approved
0.8468	Intermediate Similarity	NPD6008	Approved
0.8435	Intermediate Similarity	NPD4632	Approved
0.8393	Intermediate Similarity	NPD5701	Approved
0.8376	Intermediate Similarity	NPD6009	Approved
0.8261	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD5983	Phase 2
0.8197	Intermediate Similarity	NPD7492	Approved
0.8182	Intermediate Similarity	NPD4696	Approved
0.8182	Intermediate Similarity	NPD5286	Approved
0.8182	Intermediate Similarity	NPD5285	Approved
0.8167	Intermediate Similarity	NPD6054	Approved
0.8151	Intermediate Similarity	NPD6335	Approved
0.8145	Intermediate Similarity	NPD7736	Approved
0.813	Intermediate Similarity	NPD6616	Approved
0.813	Intermediate Similarity	NPD6336	Discontinued
0.8108	Intermediate Similarity	NPD5223	Approved
0.8083	Intermediate Similarity	NPD7101	Approved
0.8083	Intermediate Similarity	NPD7100	Approved
0.8067	Intermediate Similarity	NPD6317	Approved
0.8065	Intermediate Similarity	NPD7078	Approved
0.8036	Intermediate Similarity	NPD5211	Phase 2
0.8036	Intermediate Similarity	NPD5226	Approved
0.8036	Intermediate Similarity	NPD5224	Approved
0.8036	Intermediate Similarity	NPD5225	Approved
0.8036	Intermediate Similarity	NPD4633	Approved
0.8033	Intermediate Similarity	NPD6370	Approved
0.8	Intermediate Similarity	NPD6314	Approved
0.8	Intermediate Similarity	NPD6313	Approved
0.8	Intermediate Similarity	NPD6083	Phase 2
0.8	Intermediate Similarity	NPD6084	Phase 2
0.8	Intermediate Similarity	NPD4755	Approved
0.7983	Intermediate Similarity	NPD6274	Approved
0.7965	Intermediate Similarity	NPD5175	Approved
0.7965	Intermediate Similarity	NPD5174	Approved
0.7951	Intermediate Similarity	NPD6016	Approved
0.7951	Intermediate Similarity	NPD6015	Approved
0.792	Intermediate Similarity	NPD8293	Discontinued
0.7909	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD5222	Approved
0.7909	Intermediate Similarity	NPD5221	Approved
0.7895	Intermediate Similarity	NPD5141	Approved
0.7886	Intermediate Similarity	NPD5988	Approved
0.787	Intermediate Similarity	NPD6079	Approved
0.7869	Intermediate Similarity	NPD6059	Approved
0.7863	Intermediate Similarity	NPD4634	Approved
0.7857	Intermediate Similarity	NPD4700	Approved
0.7845	Intermediate Similarity	NPD4729	Approved
0.7845	Intermediate Similarity	NPD4730	Approved
0.7838	Intermediate Similarity	NPD5173	Approved
0.7833	Intermediate Similarity	NPD6868	Approved
0.7805	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6399	Phase 3
0.7768	Intermediate Similarity	NPD5696	Approved
0.7748	Intermediate Similarity	NPD4697	Phase 3
0.7712	Intermediate Similarity	NPD5247	Approved
0.7712	Intermediate Similarity	NPD5251	Approved
0.7712	Intermediate Similarity	NPD5250	Approved
0.7712	Intermediate Similarity	NPD5249	Phase 3
0.7712	Intermediate Similarity	NPD5248	Approved
0.7685	Intermediate Similarity	NPD5328	Approved
0.7672	Intermediate Similarity	NPD4768	Approved
0.7672	Intermediate Similarity	NPD4767	Approved
0.7661	Intermediate Similarity	NPD6909	Approved
0.7661	Intermediate Similarity	NPD6908	Approved
0.7658	Intermediate Similarity	NPD5695	Phase 3
0.7658	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD4754	Approved
0.7623	Intermediate Similarity	NPD7115	Discovery
0.7611	Intermediate Similarity	NPD7638	Approved
0.7593	Intermediate Similarity	NPD5737	Approved
0.7593	Intermediate Similarity	NPD6672	Approved
0.7563	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD5135	Approved
0.7563	Intermediate Similarity	NPD5169	Approved
0.7544	Intermediate Similarity	NPD7639	Approved
0.7544	Intermediate Similarity	NPD7640	Approved
0.7542	Intermediate Similarity	NPD5128	Approved
0.754	Intermediate Similarity	NPD8328	Phase 3
0.7523	Intermediate Similarity	NPD6673	Approved
0.7523	Intermediate Similarity	NPD6080	Approved
0.7523	Intermediate Similarity	NPD6904	Approved
0.7522	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD5127	Approved
0.75	Intermediate Similarity	NPD5217	Approved
0.75	Intermediate Similarity	NPD5216	Approved
0.75	Intermediate Similarity	NPD5210	Approved
0.7477	Intermediate Similarity	NPD4202	Approved
0.7442	Intermediate Similarity	NPD6033	Approved
0.7411	Intermediate Similarity	NPD7748	Approved
0.7411	Intermediate Similarity	NPD6001	Approved
0.7407	Intermediate Similarity	NPD3618	Phase 1
0.7407	Intermediate Similarity	NPD7334	Approved
0.7407	Intermediate Similarity	NPD7146	Approved
0.7407	Intermediate Similarity	NPD5330	Approved
0.7407	Intermediate Similarity	NPD6409	Approved
0.7407	Intermediate Similarity	NPD7521	Approved
0.7407	Intermediate Similarity	NPD6684	Approved
0.7364	Intermediate Similarity	NPD4753	Phase 2
0.7333	Intermediate Similarity	NPD6333	Approved
0.7333	Intermediate Similarity	NPD6334	Approved
0.7317	Intermediate Similarity	NPD5167	Approved
0.7311	Intermediate Similarity	NPD6412	Phase 2
0.7287	Intermediate Similarity	NPD7507	Approved
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6903	Approved
0.7257	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7900	Approved
0.725	Intermediate Similarity	NPD5168	Approved
0.7248	Intermediate Similarity	NPD6098	Approved
0.7232	Intermediate Similarity	NPD7515	Phase 2
0.7232	Intermediate Similarity	NPD5284	Approved
0.7232	Intermediate Similarity	NPD5693	Phase 1
0.7232	Intermediate Similarity	NPD8035	Phase 2
0.7232	Intermediate Similarity	NPD6050	Approved
0.7232	Intermediate Similarity	NPD5281	Approved
0.7232	Intermediate Similarity	NPD5694	Approved
0.7232	Intermediate Similarity	NPD8034	Phase 2
0.7222	Intermediate Similarity	NPD3133	Approved
0.7222	Intermediate Similarity	NPD3665	Phase 1
0.7222	Intermediate Similarity	NPD3666	Approved
0.7222	Intermediate Similarity	NPD4786	Approved
0.72	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5329	Approved
0.7154	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7131	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7319	Approved
0.7091	Intermediate Similarity	NPD5690	Phase 2
0.7064	Intermediate Similarity	NPD4197	Approved
0.7049	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3667	Approved
0.7027	Intermediate Similarity	NPD3573	Approved
0.7025	Intermediate Similarity	NPD6614	Approved
0.7015	Intermediate Similarity	NPD7260	Phase 2
0.6975	Remote Similarity	NPD7632	Discontinued
0.6967	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5279	Phase 3
0.6923	Remote Similarity	NPD5959	Approved
0.6911	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4221	Approved
0.6881	Remote Similarity	NPD4223	Phase 3
0.687	Remote Similarity	NPD6067	Discontinued
0.6847	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7503	Approved
0.6846	Remote Similarity	NPD8033	Approved
0.6842	Remote Similarity	NPD5207	Approved
0.6829	Remote Similarity	NPD6686	Approved
0.6815	Remote Similarity	NPD5956	Approved
0.6814	Remote Similarity	NPD5208	Approved
0.6786	Remote Similarity	NPD4694	Approved
0.6786	Remote Similarity	NPD5280	Approved
0.6783	Remote Similarity	NPD6411	Approved
0.6769	Remote Similarity	NPD8294	Approved
0.6769	Remote Similarity	NPD8377	Approved
0.6752	Remote Similarity	NPD5654	Approved
0.6744	Remote Similarity	NPD7327	Approved
0.6744	Remote Similarity	NPD7328	Approved
0.6727	Remote Similarity	NPD6435	Approved
0.672	Remote Similarity	NPD6371	Approved
0.6718	Remote Similarity	NPD8335	Approved
0.6718	Remote Similarity	NPD8380	Approved
0.6718	Remote Similarity	NPD8378	Approved
0.6718	Remote Similarity	NPD8379	Approved
0.6718	Remote Similarity	NPD8296	Approved
0.6712	Remote Similarity	NPD7236	Approved
0.6697	Remote Similarity	NPD4695	Discontinued
0.6696	Remote Similarity	NPD5785	Approved
0.6694	Remote Similarity	NPD5091	Approved
0.6692	Remote Similarity	NPD7516	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