NPASS Compound

Structure

NPC231589 OpenBabel07101718322D 41 45 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 -0.0000 -2.0000 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 -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 2 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 1 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 -0.8660 -1.5000 0.0000 C 0 0 1 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 0.8660 -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 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 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 2 19 2 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 31 1 0 0 0 0 9 10 1 0 0 0 0 9 24 1 0 0 0 0 10 27 1 0 0 0 0 11 12 2 0 0 0 0 11 25 1 0 0 0 0 12 33 1 0 0 0 0 13 14 1 0 0 0 0 13 31 1 0 0 0 0 15 26 1 0 0 0 0 15 32 1 0 0 0 0 16 18 1 0 0 0 0 16 35 1 0 0 0 0 17 33 1 0 0 0 0 17 34 1 0 0 0 0 18 1 1 1 0 0 0 18 19 1 0 0 0 0 19 29 1 0 0 0 0 20 3 1 6 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 4 1 1 0 0 0 21 28 1 0 0 0 0 21 30 1 0 0 0 0 22 36 2 0 0 0 0 22 40 1 0 0 0 0 23 37 2 0 0 0 0 23 41 1 0 0 0 0 24 33 1 1 0 0 0 25 38 2 0 0 0 0 26 28 1 0 0 0 0 26 40 1 1 0 0 0 27 32 1 6 0 0 0 27 34 1 0 0 0 0 28 31 1 1 0 0 0 29 39 2 0 0 0 0 30 29 1 1 0 0 0 30 41 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 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.34
Volume:	599.55
LogP:	3.61
LogD:	2.953
LogS:	-4.524
# Rotatable Bonds:	10
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	6.249
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:	-5.159
MDCK Permeability:	1.842702658905182e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.535
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.439
Plasma Protein Binding (PPB):	81.88408660888672%
Volume Distribution (VD):	0.991
Pgp-substrate:	15.6397705078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.149
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.651
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.594

ADMET: Excretion

Clearance (CL):	3.265
Half-life (T1/2):	0.286

ADMET: Toxicity

hERG Blockers:	0.444
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.645
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.894
Carcinogencity:	0.782
Eye Corrosion:	0.007
Eye Irritation:	0.012
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC231589

Natural Product ID:	NPC231589
*Common Name:**	TWPRESPPOZCYON-GTRHSOFTSA-N
IUPAC Name:	n.a.
Synonyms:	25-Epi-Neoboutomellerone
Standard InCHIKey:	TWPRESPPOZCYON-GTRHSOFTSA-N
Standard InCHI:	InChI=1S/C34H48O7/c1-18(16-35)19(2)29(39)30(41-23(6)37)21(4)28-26(40-22(5)36)15-32(8)27-10-9-24-20(3)25(38)11-12-33(24)17-34(27,33)14-13-31(28,32)7/h11-12,18,20-21,24,26-28,30,35H,2,9-10,13-17H2,1,3-8H3/t18-,20+,21+,24+,26+,27+,28+,30-,31-,32+,33-,34+/m1/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]2CC[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:	CHEMBL1941160
PubChem CID:	57332097
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
Others	7

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	88.0	n.a.	PMID[479439]
NPT2	Others	Unspecified	FC	=	51.0	n.a.	PMID[479439]
NPT2	Others	Unspecified	FC	=	1.1	n.a.	PMID[479439]
NPT2	Others	Unspecified	FC	=	60.0	n.a.	PMID[479440]
NPT2	Others	Unspecified	FC	=	71.0	n.a.	PMID[479440]
NPT2	Others	Unspecified	FC	=	1.5	n.a.	PMID[479440]
NPT2	Others	Unspecified	FC	=	1.0	n.a.	PMID[479440]

☑ 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 NPC231589 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	218
0.1-0.2	1333
0.2-0.3	5061
0.3-0.4	9841
0.4-0.5	11138
0.5-0.6	6346
0.6-0.7	6416
0.7-0.8	2184
0.8-0.85	127
0.85-0.9	17
0.9-0.95	6
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC118860
1.0	High Similarity	NPC214797
0.9903	High Similarity	NPC170487
0.9804	High Similarity	NPC241927
0.9804	High Similarity	NPC258543
0.9623	High Similarity	NPC270958
0.9524	High Similarity	NPC71348
0.9515	High Similarity	NPC470269
0.951	High Similarity	NPC181265
0.9444	High Similarity	NPC118638
0.9434	High Similarity	NPC202889
0.9412	High Similarity	NPC235889
0.9223	High Similarity	NPC310586
0.9216	High Similarity	NPC308351
0.9216	High Similarity	NPC271266
0.9029	High Similarity	NPC15396
0.8972	High Similarity	NPC197428
0.8952	High Similarity	NPC470267
0.8879	High Similarity	NPC304495
0.8785	High Similarity	NPC94529
0.8774	High Similarity	NPC196528
0.8774	High Similarity	NPC470309
0.8739	High Similarity	NPC148458
0.8716	High Similarity	NPC470281
0.8692	High Similarity	NPC44063
0.8679	High Similarity	NPC29705
0.8661	High Similarity	NPC239273
0.8654	High Similarity	NPC218383
0.8636	High Similarity	NPC100267
0.8636	High Similarity	NPC475524
0.8611	High Similarity	NPC211224
0.8598	High Similarity	NPC278628
0.8598	High Similarity	NPC231530
0.8598	High Similarity	NPC96377
0.8585	High Similarity	NPC140723
0.8545	High Similarity	NPC43775
0.8544	High Similarity	NPC42042
0.8532	High Similarity	NPC2766
0.8519	High Similarity	NPC475294
0.8505	High Similarity	NPC255309
0.8482	Intermediate Similarity	NPC471398
0.8468	Intermediate Similarity	NPC221144
0.8468	Intermediate Similarity	NPC280782
0.8447	Intermediate Similarity	NPC469599
0.8426	Intermediate Similarity	NPC475571
0.8393	Intermediate Similarity	NPC472926
0.8393	Intermediate Similarity	NPC52634
0.8381	Intermediate Similarity	NPC114274
0.8365	Intermediate Similarity	NPC58052
0.8365	Intermediate Similarity	NPC111684
0.8333	Intermediate Similarity	NPC164835
0.8333	Intermediate Similarity	NPC471854
0.8333	Intermediate Similarity	NPC472927
0.8333	Intermediate Similarity	NPC154101
0.8333	Intermediate Similarity	NPC228669
0.8333	Intermediate Similarity	NPC96268
0.8333	Intermediate Similarity	NPC137657
0.8318	Intermediate Similarity	NPC22388
0.8318	Intermediate Similarity	NPC87351
0.8302	Intermediate Similarity	NPC474720
0.8286	Intermediate Similarity	NPC108078
0.8286	Intermediate Similarity	NPC87090
0.8261	Intermediate Similarity	NPC311554
0.8261	Intermediate Similarity	NPC257457
0.8257	Intermediate Similarity	NPC265127
0.8252	Intermediate Similarity	NPC109414
0.8252	Intermediate Similarity	NPC206810
0.8241	Intermediate Similarity	NPC159442
0.8241	Intermediate Similarity	NPC311612
0.8241	Intermediate Similarity	NPC236390
0.823	Intermediate Similarity	NPC962
0.823	Intermediate Similarity	NPC194100
0.8224	Intermediate Similarity	NPC477356
0.8224	Intermediate Similarity	NPC476223
0.8224	Intermediate Similarity	NPC224720
0.8224	Intermediate Similarity	NPC476240
0.8224	Intermediate Similarity	NPC474327
0.8208	Intermediate Similarity	NPC477854
0.8208	Intermediate Similarity	NPC271387
0.8208	Intermediate Similarity	NPC197386
0.8208	Intermediate Similarity	NPC153792
0.819	Intermediate Similarity	NPC472933
0.819	Intermediate Similarity	NPC49371
0.819	Intermediate Similarity	NPC319570
0.819	Intermediate Similarity	NPC473203
0.8182	Intermediate Similarity	NPC3316
0.8182	Intermediate Similarity	NPC144854
0.8173	Intermediate Similarity	NPC294266
0.8167	Intermediate Similarity	NPC473253
0.8151	Intermediate Similarity	NPC473255
0.8148	Intermediate Similarity	NPC473928
0.8148	Intermediate Similarity	NPC136289
0.8148	Intermediate Similarity	NPC204450
0.8148	Intermediate Similarity	NPC56498
0.8148	Intermediate Similarity	NPC195290
0.8148	Intermediate Similarity	NPC118405
0.8142	Intermediate Similarity	NPC234042
0.8142	Intermediate Similarity	NPC152117
0.8142	Intermediate Similarity	NPC264634
0.8137	Intermediate Similarity	NPC477943
0.8136	Intermediate Similarity	NPC222688
0.8131	Intermediate Similarity	NPC144956
0.8131	Intermediate Similarity	NPC476274
0.8131	Intermediate Similarity	NPC15390
0.8131	Intermediate Similarity	NPC472972
0.8131	Intermediate Similarity	NPC167974
0.8125	Intermediate Similarity	NPC129689
0.812	Intermediate Similarity	NPC109973
0.8115	Intermediate Similarity	NPC213634
0.8113	Intermediate Similarity	NPC107243
0.8113	Intermediate Similarity	NPC57416
0.8108	Intermediate Similarity	NPC154608
0.8108	Intermediate Similarity	NPC192813
0.8108	Intermediate Similarity	NPC277017
0.8087	Intermediate Similarity	NPC49492
0.8087	Intermediate Similarity	NPC190286
0.8087	Intermediate Similarity	NPC298278
0.8087	Intermediate Similarity	NPC266728
0.8083	Intermediate Similarity	NPC93368
0.8083	Intermediate Similarity	NPC15095
0.8077	Intermediate Similarity	NPC25750
0.8073	Intermediate Similarity	NPC275583
0.8073	Intermediate Similarity	NPC470310
0.8073	Intermediate Similarity	NPC111323
0.807	Intermediate Similarity	NPC250109
0.807	Intermediate Similarity	NPC472929
0.8056	Intermediate Similarity	NPC81530
0.8056	Intermediate Similarity	NPC99411
0.8053	Intermediate Similarity	NPC207689
0.8053	Intermediate Similarity	NPC115303
0.8051	Intermediate Similarity	NPC42675
0.8049	Intermediate Similarity	NPC471855
0.8037	Intermediate Similarity	NPC98868
0.8037	Intermediate Similarity	NPC222011
0.8037	Intermediate Similarity	NPC176845
0.8037	Intermediate Similarity	NPC477355
0.8036	Intermediate Similarity	NPC286174
0.8036	Intermediate Similarity	NPC77947
0.8036	Intermediate Similarity	NPC470257
0.8034	Intermediate Similarity	NPC476960
0.8034	Intermediate Similarity	NPC475041
0.8033	Intermediate Similarity	NPC470880
0.8019	Intermediate Similarity	NPC305483
0.8019	Intermediate Similarity	NPC200054
0.8019	Intermediate Similarity	NPC477853
0.8019	Intermediate Similarity	NPC96859
0.8019	Intermediate Similarity	NPC125622
0.8019	Intermediate Similarity	NPC328162
0.8019	Intermediate Similarity	NPC29410
0.8019	Intermediate Similarity	NPC173272
0.8018	Intermediate Similarity	NPC58370
0.8018	Intermediate Similarity	NPC220974
0.8018	Intermediate Similarity	NPC43285
0.8018	Intermediate Similarity	NPC472925
0.8018	Intermediate Similarity	NPC185
0.8018	Intermediate Similarity	NPC59530
0.8017	Intermediate Similarity	NPC473265
0.8017	Intermediate Similarity	NPC472934
0.8017	Intermediate Similarity	NPC152091
0.8017	Intermediate Similarity	NPC470882
0.8	Intermediate Similarity	NPC135854
0.8	Intermediate Similarity	NPC2436
0.8	Intermediate Similarity	NPC196485
0.8	Intermediate Similarity	NPC216245
0.8	Intermediate Similarity	NPC245972
0.8	Intermediate Similarity	NPC111015
0.8	Intermediate Similarity	NPC470251
0.8	Intermediate Similarity	NPC474181
0.8	Intermediate Similarity	NPC28656
0.8	Intermediate Similarity	NPC473798
0.8	Intermediate Similarity	NPC123117
0.7984	Intermediate Similarity	NPC469674
0.7984	Intermediate Similarity	NPC58029
0.7982	Intermediate Similarity	NPC147180
0.7982	Intermediate Similarity	NPC119601
0.7982	Intermediate Similarity	NPC308726
0.7982	Intermediate Similarity	NPC236217
0.7982	Intermediate Similarity	NPC477054
0.7982	Intermediate Similarity	NPC53222
0.7982	Intermediate Similarity	NPC475320
0.7981	Intermediate Similarity	NPC218301
0.7966	Intermediate Similarity	NPC79579
0.7965	Intermediate Similarity	NPC321556
0.7965	Intermediate Similarity	NPC76084
0.7965	Intermediate Similarity	NPC206595
0.7965	Intermediate Similarity	NPC6206
0.7965	Intermediate Similarity	NPC5284
0.7965	Intermediate Similarity	NPC163314
0.7963	Intermediate Similarity	NPC205899
0.7963	Intermediate Similarity	NPC83709
0.7963	Intermediate Similarity	NPC241221
0.7961	Intermediate Similarity	NPC305039
0.7961	Intermediate Similarity	NPC54689
0.7961	Intermediate Similarity	NPC186688
0.7949	Intermediate Similarity	NPC153440
0.7946	Intermediate Similarity	NPC275539
0.7946	Intermediate Similarity	NPC189075
0.7946	Intermediate Similarity	NPC469844
0.7944	Intermediate Similarity	NPC69385
0.7944	Intermediate Similarity	NPC18509

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 NPC231589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1564
0.2-0.3	3931
0.3-0.4	2304
0.4-0.5	653
0.5-0.6	205
0.6-0.7	144
0.7-0.8	124
0.8-0.85	33
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8785	High Similarity	NPD6881	Approved
0.8785	High Similarity	NPD6899	Approved
0.8716	High Similarity	NPD6649	Approved
0.8716	High Similarity	NPD6650	Approved
0.8716	High Similarity	NPD8130	Phase 1
0.8692	High Similarity	NPD5697	Approved
0.8636	High Similarity	NPD8297	Approved
0.8624	High Similarity	NPD6883	Approved
0.8624	High Similarity	NPD7290	Approved
0.8624	High Similarity	NPD7102	Approved
0.8611	High Similarity	NPD6011	Approved
0.8598	High Similarity	NPD6675	Approved
0.8598	High Similarity	NPD5739	Approved
0.8598	High Similarity	NPD6402	Approved
0.8598	High Similarity	NPD7128	Approved
0.8545	High Similarity	NPD6847	Approved
0.8545	High Similarity	NPD6617	Approved
0.8545	High Similarity	NPD6869	Approved
0.8534	High Similarity	NPD7604	Phase 2
0.8532	High Similarity	NPD6373	Approved
0.8532	High Similarity	NPD6372	Approved
0.8532	High Similarity	NPD6013	Approved
0.8532	High Similarity	NPD6012	Approved
0.8532	High Similarity	NPD6014	Approved
0.8468	Intermediate Similarity	NPD6882	Approved
0.8462	Intermediate Similarity	NPD6083	Phase 2
0.8462	Intermediate Similarity	NPD6084	Phase 2
0.844	Intermediate Similarity	NPD7320	Approved
0.8393	Intermediate Similarity	NPD4632	Approved
0.8349	Intermediate Similarity	NPD5701	Approved
0.8333	Intermediate Similarity	NPD6009	Approved
0.8276	Intermediate Similarity	NPD6319	Approved
0.8257	Intermediate Similarity	NPD6008	Approved
0.8214	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD5696	Approved
0.8205	Intermediate Similarity	NPD5983	Phase 2
0.8151	Intermediate Similarity	NPD7492	Approved
0.8131	Intermediate Similarity	NPD4696	Approved
0.8131	Intermediate Similarity	NPD5286	Approved
0.8131	Intermediate Similarity	NPD5285	Approved
0.812	Intermediate Similarity	NPD6054	Approved
0.8103	Intermediate Similarity	NPD6335	Approved
0.8099	Intermediate Similarity	NPD7736	Approved
0.8095	Intermediate Similarity	NPD5695	Phase 3
0.8083	Intermediate Similarity	NPD6616	Approved
0.8083	Intermediate Similarity	NPD6336	Discontinued
0.8077	Intermediate Similarity	NPD6399	Phase 3
0.8056	Intermediate Similarity	NPD5223	Approved
0.8039	Intermediate Similarity	NPD6672	Approved
0.8039	Intermediate Similarity	NPD5737	Approved
0.8034	Intermediate Similarity	NPD7101	Approved
0.8034	Intermediate Similarity	NPD7100	Approved
0.8017	Intermediate Similarity	NPD6317	Approved
0.8017	Intermediate Similarity	NPD7078	Approved
0.7983	Intermediate Similarity	NPD6370	Approved
0.7982	Intermediate Similarity	NPD5224	Approved
0.7982	Intermediate Similarity	NPD5211	Phase 2
0.7982	Intermediate Similarity	NPD5226	Approved
0.7982	Intermediate Similarity	NPD4633	Approved
0.7982	Intermediate Similarity	NPD5225	Approved
0.7961	Intermediate Similarity	NPD6673	Approved
0.7961	Intermediate Similarity	NPD6080	Approved
0.7961	Intermediate Similarity	NPD6904	Approved
0.7949	Intermediate Similarity	NPD6313	Approved
0.7949	Intermediate Similarity	NPD6314	Approved
0.7944	Intermediate Similarity	NPD4755	Approved
0.7931	Intermediate Similarity	NPD6274	Approved
0.7925	Intermediate Similarity	NPD4629	Approved
0.7925	Intermediate Similarity	NPD5210	Approved
0.7909	Intermediate Similarity	NPD5175	Approved
0.7909	Intermediate Similarity	NPD5174	Approved
0.7899	Intermediate Similarity	NPD6016	Approved
0.7899	Intermediate Similarity	NPD6015	Approved
0.7869	Intermediate Similarity	NPD8293	Discontinued
0.785	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD5221	Approved
0.785	Intermediate Similarity	NPD5222	Approved
0.7843	Intermediate Similarity	NPD6684	Approved
0.7843	Intermediate Similarity	NPD7146	Approved
0.7843	Intermediate Similarity	NPD7334	Approved
0.7843	Intermediate Similarity	NPD6409	Approved
0.7843	Intermediate Similarity	NPD7521	Approved
0.7843	Intermediate Similarity	NPD5330	Approved
0.7838	Intermediate Similarity	NPD5141	Approved
0.7833	Intermediate Similarity	NPD5988	Approved
0.7815	Intermediate Similarity	NPD6059	Approved
0.781	Intermediate Similarity	NPD6079	Approved
0.7807	Intermediate Similarity	NPD4634	Approved
0.7798	Intermediate Similarity	NPD4700	Approved
0.7788	Intermediate Similarity	NPD4753	Phase 2
0.7778	Intermediate Similarity	NPD6868	Approved
0.7778	Intermediate Similarity	NPD5173	Approved
0.7757	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD6412	Phase 2
0.7692	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6903	Approved
0.7685	Intermediate Similarity	NPD4697	Phase 3
0.767	Intermediate Similarity	NPD6098	Approved
0.7647	Intermediate Similarity	NPD3133	Approved
0.7647	Intermediate Similarity	NPD3666	Approved
0.7647	Intermediate Similarity	NPD3665	Phase 1
0.7642	Intermediate Similarity	NPD5693	Phase 1
0.7642	Intermediate Similarity	NPD5694	Approved
0.7642	Intermediate Similarity	NPD5284	Approved
0.7642	Intermediate Similarity	NPD5281	Approved
0.7642	Intermediate Similarity	NPD6050	Approved
0.7632	Intermediate Similarity	NPD4729	Approved
0.7632	Intermediate Similarity	NPD4730	Approved
0.7619	Intermediate Similarity	NPD5328	Approved
0.7603	Intermediate Similarity	NPD6908	Approved
0.7603	Intermediate Similarity	NPD6909	Approved
0.7589	Intermediate Similarity	NPD4754	Approved
0.7573	Intermediate Similarity	NPD5329	Approved
0.7547	Intermediate Similarity	NPD5692	Phase 3
0.7545	Intermediate Similarity	NPD7638	Approved
0.7521	Intermediate Similarity	NPD6053	Discontinued
0.75	Intermediate Similarity	NPD5247	Approved
0.75	Intermediate Similarity	NPD5250	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD5249	Phase 3
0.75	Intermediate Similarity	NPD5248	Approved
0.75	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5169	Approved
0.75	Intermediate Similarity	NPD5251	Approved
0.75	Intermediate Similarity	NPD5135	Approved
0.7478	Intermediate Similarity	NPD5128	Approved
0.7477	Intermediate Similarity	NPD7640	Approved
0.7477	Intermediate Similarity	NPD7639	Approved
0.7476	Intermediate Similarity	NPD4786	Approved
0.7476	Intermediate Similarity	NPD4197	Approved
0.7456	Intermediate Similarity	NPD4767	Approved
0.7456	Intermediate Similarity	NPD4768	Approved
0.7455	Intermediate Similarity	NPD7902	Approved
0.7436	Intermediate Similarity	NPD5127	Approved
0.7436	Intermediate Similarity	NPD5216	Approved
0.7436	Intermediate Similarity	NPD5215	Approved
0.7436	Intermediate Similarity	NPD5217	Approved
0.7417	Intermediate Similarity	NPD7115	Discovery
0.7407	Intermediate Similarity	NPD4202	Approved
0.7391	Intermediate Similarity	NPD6614	Approved
0.7381	Intermediate Similarity	NPD6033	Approved
0.7339	Intermediate Similarity	NPD7748	Approved
0.7339	Intermediate Similarity	NPD8328	Phase 3
0.7339	Intermediate Similarity	NPD6001	Approved
0.7333	Intermediate Similarity	NPD5279	Phase 3
0.7333	Intermediate Similarity	NPD3618	Phase 1
0.7297	Intermediate Similarity	NPD5959	Approved
0.7282	Intermediate Similarity	NPD3667	Approved
0.7282	Intermediate Similarity	NPD4223	Phase 3
0.7282	Intermediate Similarity	NPD4221	Approved
0.7273	Intermediate Similarity	NPD6334	Approved
0.7273	Intermediate Similarity	NPD6333	Approved
0.725	Intermediate Similarity	NPD5167	Approved
0.7222	Intermediate Similarity	NPD5207	Approved
0.7196	Intermediate Similarity	NPD5208	Approved
0.7182	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7900	Approved
0.7179	Intermediate Similarity	NPD5168	Approved
0.717	Intermediate Similarity	NPD5280	Approved
0.717	Intermediate Similarity	NPD4694	Approved
0.7156	Intermediate Similarity	NPD7515	Phase 2
0.7156	Intermediate Similarity	NPD8035	Phase 2
0.7156	Intermediate Similarity	NPD8034	Phase 2
0.7132	Intermediate Similarity	NPD5956	Approved
0.7117	Intermediate Similarity	NPD5654	Approved
0.7115	Intermediate Similarity	NPD6435	Approved
0.7087	Intermediate Similarity	NPD7507	Approved
0.7087	Intermediate Similarity	NPD4695	Discontinued
0.7077	Intermediate Similarity	NPD7260	Phase 2
0.7064	Intermediate Similarity	NPD5785	Approved
0.7059	Intermediate Similarity	NPD6371	Approved
0.7048	Intermediate Similarity	NPD4788	Approved
0.7043	Intermediate Similarity	NPD5091	Approved
0.7034	Intermediate Similarity	NPD6686	Approved
0.7016	Intermediate Similarity	NPD4522	Approved
0.7009	Intermediate Similarity	NPD5205	Approved
0.7009	Intermediate Similarity	NPD4688	Approved
0.7009	Intermediate Similarity	NPD4689	Approved
0.7009	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4690	Approved
0.7009	Intermediate Similarity	NPD4693	Phase 3
0.7009	Intermediate Similarity	NPD4138	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.6992	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4195	Approved
0.6972	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3573	Approved
0.6937	Remote Similarity	NPD5133	Approved
0.6923	Remote Similarity	NPD5368	Approved
0.6923	Remote Similarity	NPD7319	Approved
0.6916	Remote Similarity	NPD5363	Approved
0.6897	Remote Similarity	NPD7632	Discontinued
0.6893	Remote Similarity	NPD3617	Approved
0.6891	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5282	Discontinued
0.6857	Remote Similarity	NPD5369	Approved
0.6852	Remote Similarity	NPD5786	Approved
0.6847	Remote Similarity	NPD7637	Suspended
0.6838	Remote Similarity	NPD6052	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