NPASS Compound

Structure

NPC170487 OpenBabel07101718272D 42 46 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 -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 -0.0000 1.0000 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 2.6831 -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 1.3253 1.9135 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 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 -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 1.7321 1.0000 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 0.3308 2.0181 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 8 9 1 0 0 0 0 8 24 1 0 0 0 0 9 27 1 0 0 0 0 10 11 2 0 0 0 0 10 25 1 0 0 0 0 11 32 1 0 0 0 0 12 13 1 0 0 0 0 13 34 1 0 0 0 0 14 26 1 0 0 0 0 14 31 1 0 0 0 0 15 18 1 0 0 0 0 15 35 1 0 0 0 0 16 32 1 0 0 0 0 16 33 1 0 0 0 0 17 36 1 0 0 0 0 18 1 1 6 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 37 2 0 0 0 0 22 41 1 0 0 0 0 23 38 2 0 0 0 0 23 42 1 0 0 0 0 24 32 1 1 0 0 0 25 39 2 0 0 0 0 26 28 1 0 0 0 0 26 41 1 1 0 0 0 27 31 1 6 0 0 0 27 33 1 0 0 0 0 28 34 1 1 0 0 0 29 40 2 0 0 0 0 30 29 1 1 0 0 0 30 42 1 0 0 0 0 31 34 1 6 0 0 0 32 33 1 6 0 0 0 33 12 1 6 0 0 0 34 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.33
Volume:	608.341
LogP:	2.354
LogD:	1.841
LogS:	-4.433
# Rotatable Bonds:	11
TPSA:	127.2
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.305
Synthetic Accessibility Score:	6.37
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:	-5.405
MDCK Permeability:	2.498949834262021e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.101
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.454
Plasma Protein Binding (PPB):	80.96019744873047%
Volume Distribution (VD):	0.874
Pgp-substrate:	13.856681823730469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.415
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.573

ADMET: Excretion

Clearance (CL):	2.669
Half-life (T1/2):	0.435

ADMET: Toxicity

hERG Blockers:	0.52
Human Hepatotoxicity (H-HT):	0.305
Drug-inuced Liver Injury (DILI):	0.533
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.915
Carcinogencity:	0.834
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC170487

Natural Product ID:	NPC170487
*Common Name:**	OWFOMRNWEYWSEL-FDQMDRLDSA-N
IUPAC Name:	n.a.
Synonyms:	18-Hydroxyneoboutomellerone
Standard InCHIKey:	OWFOMRNWEYWSEL-FDQMDRLDSA-N
Standard InCHI:	InChI=1S/C34H48O8/c1-18(15-35)19(2)29(40)30(42-23(6)38)21(4)28-26(41-22(5)37)14-31(7)27-9-8-24-20(3)25(39)10-11-32(24)16-33(27,32)12-13-34(28,31)17-36/h10-11,18,20-21,24,26-28,30,35-36H,2,8-9,12-17H2,1,3-7H3/t18-,20-,21-,24-,26-,27-,28-,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(CO)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:	CHEMBL1941158
PubChem CID:	57331961
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	6

Activity Type	# Activity
Others	6

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	1.1	n.a.	PMID[508846]
NPT2	Others	Unspecified	FC	=	12.0	n.a.	PMID[508846]
NPT2	Others	Unspecified	FC	=	1.2	n.a.	PMID[508846]
NPT2	Others	Unspecified	FC	=	1.1	n.a.	PMID[508847]
NPT2	Others	Unspecified	FC	=	12.0	n.a.	PMID[508847]
NPT2	Others	Unspecified	FC	=	1.2	n.a.	PMID[508847]

☑ 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 NPC170487 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	224
0.1-0.2	1346
0.2-0.3	5105
0.3-0.4	9868
0.4-0.5	11075
0.5-0.6	6361
0.6-0.7	6364
0.7-0.8	2195
0.8-0.85	129
0.85-0.9	14
0.9-0.95	7
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC214797
0.9903	High Similarity	NPC118860
0.9903	High Similarity	NPC231589
0.9717	High Similarity	NPC270958
0.9709	High Similarity	NPC258543
0.9709	High Similarity	NPC241927
0.9612	High Similarity	NPC470269
0.9537	High Similarity	NPC118638
0.9528	High Similarity	NPC202889
0.9434	High Similarity	NPC71348
0.9417	High Similarity	NPC181265
0.932	High Similarity	NPC235889
0.9135	High Similarity	NPC310586
0.9126	High Similarity	NPC308351
0.9126	High Similarity	NPC271266
0.8972	High Similarity	NPC304495
0.8942	High Similarity	NPC15396
0.8889	High Similarity	NPC197428
0.8868	High Similarity	NPC470267
0.8868	High Similarity	NPC196528
0.8829	High Similarity	NPC148458
0.8807	High Similarity	NPC470281
0.875	High Similarity	NPC239273
0.8727	High Similarity	NPC475524
0.8727	High Similarity	NPC100267
0.8704	High Similarity	NPC94529
0.8692	High Similarity	NPC470309
0.8611	High Similarity	NPC44063
0.8598	High Similarity	NPC29705
0.8571	High Similarity	NPC218383
0.8559	High Similarity	NPC221144
0.8559	High Similarity	NPC280782
0.8532	High Similarity	NPC211224
0.8519	High Similarity	NPC231530
0.8519	High Similarity	NPC278628
0.8519	High Similarity	NPC475571
0.8519	High Similarity	NPC96377
0.8505	High Similarity	NPC140723
0.8482	Intermediate Similarity	NPC52634
0.8482	Intermediate Similarity	NPC472926
0.8468	Intermediate Similarity	NPC43775
0.8462	Intermediate Similarity	NPC42042
0.8455	Intermediate Similarity	NPC2766
0.844	Intermediate Similarity	NPC475294
0.8426	Intermediate Similarity	NPC255309
0.8421	Intermediate Similarity	NPC471854
0.8421	Intermediate Similarity	NPC472927
0.8407	Intermediate Similarity	NPC471398
0.8365	Intermediate Similarity	NPC469599
0.8348	Intermediate Similarity	NPC311554
0.8348	Intermediate Similarity	NPC257457
0.8319	Intermediate Similarity	NPC962
0.8302	Intermediate Similarity	NPC114274
0.8286	Intermediate Similarity	NPC111684
0.8286	Intermediate Similarity	NPC58052
0.8276	Intermediate Similarity	NPC472933
0.8276	Intermediate Similarity	NPC473203
0.8276	Intermediate Similarity	NPC319570
0.8257	Intermediate Similarity	NPC137657
0.8257	Intermediate Similarity	NPC228669
0.8257	Intermediate Similarity	NPC96268
0.8257	Intermediate Similarity	NPC164835
0.8252	Intermediate Similarity	NPC154101
0.8241	Intermediate Similarity	NPC22388
0.8241	Intermediate Similarity	NPC473928
0.8241	Intermediate Similarity	NPC87351
0.8235	Intermediate Similarity	NPC473255
0.823	Intermediate Similarity	NPC264634
0.8224	Intermediate Similarity	NPC474720
0.822	Intermediate Similarity	NPC222688
0.8214	Intermediate Similarity	NPC129689
0.8208	Intermediate Similarity	NPC87090
0.8208	Intermediate Similarity	NPC108078
0.8205	Intermediate Similarity	NPC109973
0.8197	Intermediate Similarity	NPC213634
0.8182	Intermediate Similarity	NPC265127
0.8174	Intermediate Similarity	NPC266728
0.8174	Intermediate Similarity	NPC49492
0.8173	Intermediate Similarity	NPC109414
0.8173	Intermediate Similarity	NPC206810
0.8167	Intermediate Similarity	NPC15095
0.8167	Intermediate Similarity	NPC93368
0.8165	Intermediate Similarity	NPC159442
0.8165	Intermediate Similarity	NPC311612
0.8165	Intermediate Similarity	NPC236390
0.8158	Intermediate Similarity	NPC250109
0.8158	Intermediate Similarity	NPC472929
0.8158	Intermediate Similarity	NPC194100
0.8148	Intermediate Similarity	NPC477356
0.8148	Intermediate Similarity	NPC224720
0.8148	Intermediate Similarity	NPC476240
0.8148	Intermediate Similarity	NPC476223
0.8148	Intermediate Similarity	NPC474327
0.8142	Intermediate Similarity	NPC115303
0.8136	Intermediate Similarity	NPC42675
0.8131	Intermediate Similarity	NPC197386
0.8131	Intermediate Similarity	NPC153792
0.8131	Intermediate Similarity	NPC271387
0.8131	Intermediate Similarity	NPC477854
0.813	Intermediate Similarity	NPC471855
0.8125	Intermediate Similarity	NPC470257
0.8125	Intermediate Similarity	NPC286174
0.8125	Intermediate Similarity	NPC77947
0.8115	Intermediate Similarity	NPC470880
0.8113	Intermediate Similarity	NPC49371
0.8108	Intermediate Similarity	NPC3316
0.8108	Intermediate Similarity	NPC144854
0.8108	Intermediate Similarity	NPC43285
0.8108	Intermediate Similarity	NPC58370
0.8103	Intermediate Similarity	NPC472934
0.8099	Intermediate Similarity	NPC473253
0.8099	Intermediate Similarity	NPC473265
0.8099	Intermediate Similarity	NPC152091
0.8099	Intermediate Similarity	NPC470882
0.8095	Intermediate Similarity	NPC294266
0.8091	Intermediate Similarity	NPC470251
0.8091	Intermediate Similarity	NPC135854
0.8091	Intermediate Similarity	NPC2436
0.8091	Intermediate Similarity	NPC216245
0.8087	Intermediate Similarity	NPC473798
0.8073	Intermediate Similarity	NPC118405
0.8073	Intermediate Similarity	NPC136289
0.8073	Intermediate Similarity	NPC195290
0.8073	Intermediate Similarity	NPC53222
0.8073	Intermediate Similarity	NPC56498
0.8073	Intermediate Similarity	NPC204450
0.807	Intermediate Similarity	NPC234042
0.807	Intermediate Similarity	NPC152117
0.807	Intermediate Similarity	NPC147180
0.8065	Intermediate Similarity	NPC58029
0.8065	Intermediate Similarity	NPC469674
0.8058	Intermediate Similarity	NPC477943
0.8056	Intermediate Similarity	NPC167974
0.8056	Intermediate Similarity	NPC15390
0.8056	Intermediate Similarity	NPC472972
0.8056	Intermediate Similarity	NPC476274
0.8056	Intermediate Similarity	NPC241221
0.8056	Intermediate Similarity	NPC144956
0.8053	Intermediate Similarity	NPC321556
0.8037	Intermediate Similarity	NPC57416
0.8037	Intermediate Similarity	NPC107243
0.8036	Intermediate Similarity	NPC277017
0.8036	Intermediate Similarity	NPC154608
0.8036	Intermediate Similarity	NPC192813
0.8018	Intermediate Similarity	NPC50535
0.8017	Intermediate Similarity	NPC328374
0.8017	Intermediate Similarity	NPC63186
0.8017	Intermediate Similarity	NPC96312
0.8017	Intermediate Similarity	NPC251236
0.8017	Intermediate Similarity	NPC190286
0.8017	Intermediate Similarity	NPC298278
0.8017	Intermediate Similarity	NPC40632
0.8	Intermediate Similarity	NPC470310
0.8	Intermediate Similarity	NPC33973
0.8	Intermediate Similarity	NPC275583
0.8	Intermediate Similarity	NPC70967
0.8	Intermediate Similarity	NPC238005
0.8	Intermediate Similarity	NPC141196
0.8	Intermediate Similarity	NPC111323
0.8	Intermediate Similarity	NPC117185
0.8	Intermediate Similarity	NPC1980
0.8	Intermediate Similarity	NPC25750
0.7984	Intermediate Similarity	NPC34963
0.7983	Intermediate Similarity	NPC310511
0.7982	Intermediate Similarity	NPC207689
0.7982	Intermediate Similarity	NPC99411
0.7982	Intermediate Similarity	NPC124211
0.7982	Intermediate Similarity	NPC472928
0.7982	Intermediate Similarity	NPC81530
0.7967	Intermediate Similarity	NPC221414
0.7967	Intermediate Similarity	NPC471407
0.7967	Intermediate Similarity	NPC35109
0.7966	Intermediate Similarity	NPC5292
0.7966	Intermediate Similarity	NPC475041
0.7966	Intermediate Similarity	NPC476960
0.7963	Intermediate Similarity	NPC222011
0.7963	Intermediate Similarity	NPC176845
0.7963	Intermediate Similarity	NPC477355
0.7963	Intermediate Similarity	NPC98868
0.7949	Intermediate Similarity	NPC153651
0.7949	Intermediate Similarity	NPC475305
0.7946	Intermediate Similarity	NPC201908
0.7946	Intermediate Similarity	NPC251824
0.7946	Intermediate Similarity	NPC472925
0.7946	Intermediate Similarity	NPC220974
0.7946	Intermediate Similarity	NPC176949
0.7946	Intermediate Similarity	NPC59530
0.7946	Intermediate Similarity	NPC86852
0.7946	Intermediate Similarity	NPC185
0.7944	Intermediate Similarity	NPC328162
0.7944	Intermediate Similarity	NPC29410
0.7944	Intermediate Similarity	NPC477853
0.7944	Intermediate Similarity	NPC305483
0.7944	Intermediate Similarity	NPC200054
0.7944	Intermediate Similarity	NPC125622
0.7944	Intermediate Similarity	NPC173272
0.7944	Intermediate Similarity	NPC96859
0.7934	Intermediate Similarity	NPC475194
0.7931	Intermediate Similarity	NPC474906
0.7931	Intermediate Similarity	NPC474181

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 NPC170487 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1580
0.2-0.3	3962
0.3-0.4	2253
0.4-0.5	643
0.5-0.6	212
0.6-0.7	155
0.7-0.8	114
0.8-0.85	31
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8807	High Similarity	NPD6649	Approved
0.8807	High Similarity	NPD6650	Approved
0.8727	High Similarity	NPD8297	Approved
0.8704	High Similarity	NPD6899	Approved
0.8704	High Similarity	NPD6881	Approved
0.8636	High Similarity	NPD8130	Phase 1
0.8624	High Similarity	NPD6372	Approved
0.8624	High Similarity	NPD6373	Approved
0.8611	High Similarity	NPD5697	Approved
0.8559	High Similarity	NPD6882	Approved
0.8545	High Similarity	NPD7102	Approved
0.8545	High Similarity	NPD6883	Approved
0.8545	High Similarity	NPD7290	Approved
0.8532	High Similarity	NPD6011	Approved
0.8519	High Similarity	NPD7128	Approved
0.8519	High Similarity	NPD6675	Approved
0.8519	High Similarity	NPD6402	Approved
0.8519	High Similarity	NPD5739	Approved
0.8468	Intermediate Similarity	NPD6847	Approved
0.8468	Intermediate Similarity	NPD6869	Approved
0.8468	Intermediate Similarity	NPD6617	Approved
0.8462	Intermediate Similarity	NPD7604	Phase 2
0.8455	Intermediate Similarity	NPD6013	Approved
0.8455	Intermediate Similarity	NPD6014	Approved
0.8455	Intermediate Similarity	NPD6012	Approved
0.8381	Intermediate Similarity	NPD6083	Phase 2
0.8381	Intermediate Similarity	NPD6084	Phase 2
0.8364	Intermediate Similarity	NPD7320	Approved
0.8362	Intermediate Similarity	NPD6319	Approved
0.8319	Intermediate Similarity	NPD4632	Approved
0.8273	Intermediate Similarity	NPD5701	Approved
0.8261	Intermediate Similarity	NPD6009	Approved
0.8182	Intermediate Similarity	NPD6008	Approved
0.8142	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD5983	Phase 2
0.8131	Intermediate Similarity	NPD5696	Approved
0.8083	Intermediate Similarity	NPD7492	Approved
0.8056	Intermediate Similarity	NPD5286	Approved
0.8056	Intermediate Similarity	NPD5285	Approved
0.8056	Intermediate Similarity	NPD4696	Approved
0.8051	Intermediate Similarity	NPD6054	Approved
0.8034	Intermediate Similarity	NPD6335	Approved
0.8033	Intermediate Similarity	NPD7736	Approved
0.8019	Intermediate Similarity	NPD5695	Phase 3
0.8017	Intermediate Similarity	NPD6616	Approved
0.8017	Intermediate Similarity	NPD6336	Discontinued
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7982	Intermediate Similarity	NPD5223	Approved
0.7966	Intermediate Similarity	NPD7100	Approved
0.7966	Intermediate Similarity	NPD7101	Approved
0.7961	Intermediate Similarity	NPD6672	Approved
0.7961	Intermediate Similarity	NPD5737	Approved
0.7951	Intermediate Similarity	NPD7078	Approved
0.7949	Intermediate Similarity	NPD6317	Approved
0.7917	Intermediate Similarity	NPD6370	Approved
0.7909	Intermediate Similarity	NPD5225	Approved
0.7909	Intermediate Similarity	NPD4633	Approved
0.7909	Intermediate Similarity	NPD5211	Phase 2
0.7909	Intermediate Similarity	NPD5224	Approved
0.7909	Intermediate Similarity	NPD5226	Approved
0.7885	Intermediate Similarity	NPD6080	Approved
0.7885	Intermediate Similarity	NPD6904	Approved
0.7885	Intermediate Similarity	NPD6673	Approved
0.7881	Intermediate Similarity	NPD6313	Approved
0.7881	Intermediate Similarity	NPD6314	Approved
0.787	Intermediate Similarity	NPD4755	Approved
0.7863	Intermediate Similarity	NPD6274	Approved
0.785	Intermediate Similarity	NPD5210	Approved
0.785	Intermediate Similarity	NPD4629	Approved
0.7838	Intermediate Similarity	NPD5175	Approved
0.7838	Intermediate Similarity	NPD5174	Approved
0.7833	Intermediate Similarity	NPD6015	Approved
0.7833	Intermediate Similarity	NPD6016	Approved
0.7805	Intermediate Similarity	NPD8293	Discontinued
0.7778	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5221	Approved
0.7778	Intermediate Similarity	NPD5222	Approved
0.7769	Intermediate Similarity	NPD5988	Approved
0.7768	Intermediate Similarity	NPD5141	Approved
0.7767	Intermediate Similarity	NPD5330	Approved
0.7767	Intermediate Similarity	NPD7521	Approved
0.7767	Intermediate Similarity	NPD7334	Approved
0.7767	Intermediate Similarity	NPD6684	Approved
0.7767	Intermediate Similarity	NPD6409	Approved
0.7767	Intermediate Similarity	NPD7146	Approved
0.775	Intermediate Similarity	NPD6059	Approved
0.7739	Intermediate Similarity	NPD4634	Approved
0.7736	Intermediate Similarity	NPD6079	Approved
0.7727	Intermediate Similarity	NPD4700	Approved
0.7719	Intermediate Similarity	NPD4730	Approved
0.7719	Intermediate Similarity	NPD4729	Approved
0.7714	Intermediate Similarity	NPD4753	Phase 2
0.7712	Intermediate Similarity	NPD6868	Approved
0.7706	Intermediate Similarity	NPD5173	Approved
0.7686	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6412	Phase 2
0.7619	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6903	Approved
0.7615	Intermediate Similarity	NPD4697	Phase 3
0.7596	Intermediate Similarity	NPD6098	Approved
0.7586	Intermediate Similarity	NPD5249	Phase 3
0.7586	Intermediate Similarity	NPD5248	Approved
0.7586	Intermediate Similarity	NPD5247	Approved
0.7586	Intermediate Similarity	NPD5251	Approved
0.7586	Intermediate Similarity	NPD5250	Approved
0.7573	Intermediate Similarity	NPD3666	Approved
0.7573	Intermediate Similarity	NPD3133	Approved
0.7573	Intermediate Similarity	NPD3665	Phase 1
0.757	Intermediate Similarity	NPD5281	Approved
0.757	Intermediate Similarity	NPD5284	Approved
0.757	Intermediate Similarity	NPD5694	Approved
0.757	Intermediate Similarity	NPD6050	Approved
0.757	Intermediate Similarity	NPD5693	Phase 1
0.7547	Intermediate Similarity	NPD5328	Approved
0.7544	Intermediate Similarity	NPD4768	Approved
0.7544	Intermediate Similarity	NPD4767	Approved
0.7541	Intermediate Similarity	NPD6908	Approved
0.7541	Intermediate Similarity	NPD6909	Approved
0.7522	Intermediate Similarity	NPD4754	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.7477	Intermediate Similarity	NPD5692	Phase 3
0.7477	Intermediate Similarity	NPD7638	Approved
0.7458	Intermediate Similarity	NPD6053	Discontinued
0.7436	Intermediate Similarity	NPD5135	Approved
0.7436	Intermediate Similarity	NPD5169	Approved
0.7436	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5690	Phase 2
0.7419	Intermediate Similarity	NPD8328	Phase 3
0.7414	Intermediate Similarity	NPD5128	Approved
0.7411	Intermediate Similarity	NPD7640	Approved
0.7411	Intermediate Similarity	NPD7639	Approved
0.7404	Intermediate Similarity	NPD4197	Approved
0.7404	Intermediate Similarity	NPD4786	Approved
0.7387	Intermediate Similarity	NPD7902	Approved
0.7373	Intermediate Similarity	NPD5217	Approved
0.7373	Intermediate Similarity	NPD5215	Approved
0.7373	Intermediate Similarity	NPD5127	Approved
0.7373	Intermediate Similarity	NPD5216	Approved
0.7355	Intermediate Similarity	NPD7115	Discovery
0.7339	Intermediate Similarity	NPD4202	Approved
0.7328	Intermediate Similarity	NPD6614	Approved
0.7323	Intermediate Similarity	NPD6033	Approved
0.7273	Intermediate Similarity	NPD6001	Approved
0.7273	Intermediate Similarity	NPD7748	Approved
0.7264	Intermediate Similarity	NPD3618	Phase 1
0.7264	Intermediate Similarity	NPD5279	Phase 3
0.7232	Intermediate Similarity	NPD5959	Approved
0.7218	Intermediate Similarity	NPD6333	Approved
0.7218	Intermediate Similarity	NPD6334	Approved
0.7212	Intermediate Similarity	NPD4223	Phase 3
0.7212	Intermediate Similarity	NPD3667	Approved
0.7212	Intermediate Similarity	NPD4221	Approved
0.719	Intermediate Similarity	NPD5167	Approved
0.7165	Intermediate Similarity	NPD7507	Approved
0.7156	Intermediate Similarity	NPD5207	Approved
0.7154	Intermediate Similarity	NPD7260	Phase 2
0.713	Intermediate Similarity	NPD5208	Approved
0.7119	Intermediate Similarity	NPD6686	Approved
0.7119	Intermediate Similarity	NPD5168	Approved
0.7117	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7900	Approved
0.7103	Intermediate Similarity	NPD5280	Approved
0.7103	Intermediate Similarity	NPD4694	Approved
0.7091	Intermediate Similarity	NPD7515	Phase 2
0.7091	Intermediate Similarity	NPD8034	Phase 2
0.7091	Intermediate Similarity	NPD8035	Phase 2
0.7077	Intermediate Similarity	NPD5956	Approved
0.7073	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5654	Approved
0.7048	Intermediate Similarity	NPD6435	Approved
0.7019	Intermediate Similarity	NPD4695	Discontinued
0.7	Intermediate Similarity	NPD7319	Approved
0.7	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD6371	Approved
0.6983	Remote Similarity	NPD5091	Approved
0.6981	Remote Similarity	NPD4788	Approved
0.696	Remote Similarity	NPD4522	Approved
0.6944	Remote Similarity	NPD4693	Phase 3
0.6944	Remote Similarity	NPD4689	Approved
0.6944	Remote Similarity	NPD4690	Approved
0.6944	Remote Similarity	NPD4138	Approved
0.6944	Remote Similarity	NPD5205	Approved
0.6944	Remote Similarity	NPD4688	Approved
0.6944	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6411	Approved
0.6923	Remote Similarity	NPD4195	Approved
0.6909	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3573	Approved
0.6875	Remote Similarity	NPD5133	Approved
0.6857	Remote Similarity	NPD5368	Approved
0.6852	Remote Similarity	NPD5363	Approved
0.685	Remote Similarity	NPD7503	Approved
0.6838	Remote Similarity	NPD7632	Discontinued
0.6833	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD3617	Approved
0.6814	Remote Similarity	NPD5282	Discontinued
0.6792	Remote Similarity	NPD5369	Approved
0.6789	Remote Similarity	NPD5786	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