NPASS Compound

Structure

NPC202889 OpenBabel07101718192D 42 46 0 0 1 0 0 0 0 0999 V2000 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7473 4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 -1.7321 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1871 5.1132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8781 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0388 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0563 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 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5909 3.0032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8270 6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0388 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0345 3.3305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2308 4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 2.7953 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 32 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 2 0 0 0 0 12 32 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 14 33 1 0 0 0 0 15 16 1 0 0 0 0 15 35 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 17 29 1 0 0 0 0 18 3 1 6 0 0 0 18 22 1 0 0 0 0 18 28 1 0 0 0 0 19 4 1 1 0 0 0 19 27 1 0 0 0 0 19 31 1 0 0 0 0 20 36 2 0 0 0 0 20 41 1 0 0 0 0 21 37 2 0 0 0 0 21 42 1 0 0 0 0 22 34 1 1 0 0 0 23 24 1 0 0 0 0 23 33 1 6 0 0 0 24 34 1 0 0 0 0 25 30 1 0 0 0 0 25 34 1 1 0 0 0 26 27 1 0 0 0 0 26 41 1 1 0 0 0 27 32 1 1 0 0 0 28 30 1 0 0 0 0 28 38 2 0 0 0 0 29 39 2 0 0 0 0 30 40 1 6 0 0 0 31 29 1 1 0 0 0 31 42 1 0 0 0 0 32 33 1 1 0 0 0 33 8 1 6 0 0 0 34 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.33
Volume:	608.341
LogP:	3.309
LogD:	1.601
LogS:	-3.434
# Rotatable Bonds:	10
TPSA:	127.2
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.247
Synthetic Accessibility Score:	6.182
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:	-5.009
MDCK Permeability:	4.2837018554564565e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.778
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.809

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.608
Plasma Protein Binding (PPB):	85.00731658935547%
Volume Distribution (VD):	1.048
Pgp-substrate:	14.374960899353027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.558
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.715
CYP3A4-substrate:	0.529

ADMET: Excretion

Clearance (CL):	4.457
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.524
Drug-inuced Liver Injury (DILI):	0.792
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.727
Skin Sensitization:	0.208
Carcinogencity:	0.397
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC202889

Natural Product ID:	NPC202889
*Common Name:**	NMKFVJYUYKWBIK-FZZFIXDZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NMKFVJYUYKWBIK-FZZFIXDZSA-N
Standard InCHI:	InChI=1S/C34H48O8/c1-16(15-35)17(2)29(39)31(42-21(6)37)19(4)27-26(41-20(5)36)14-33(8)23-10-9-22-18(3)28(38)30(40)25-13-34(22,25)24(23)11-12-32(27,33)7/h11,16,18-19,22-23,25-27,30-31,35,40H,2,9-10,12-15H2,1,3-8H3/t16-,18-,19-,22-,23+,25+,26-,27-,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=C1[C@H]2CC[C@@H]2[C@]31C[C@@H]3[C@H](C(=O)[C@H]2C)O)C)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1951414
PubChem CID:	57332909
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	15.0	n.a.	PMID[536322]
NPT2	Others	Unspecified	FC	=	1.9	n.a.	PMID[536322]
NPT2	Others	Unspecified	FC	=	1.2	n.a.	PMID[536322]

☑ 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 NPC202889 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	238
0.1-0.2	1464
0.2-0.3	5106
0.3-0.4	9571
0.4-0.5	11375
0.5-0.6	6188
0.6-0.7	5788
0.7-0.8	2722
0.8-0.85	208
0.85-0.9	24
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9811	High Similarity	NPC270958
0.963	High Similarity	NPC118638
0.9528	High Similarity	NPC170487
0.9528	High Similarity	NPC71348
0.9434	High Similarity	NPC118860
0.9434	High Similarity	NPC214797
0.9434	High Similarity	NPC231589
0.9252	High Similarity	NPC470281
0.9245	High Similarity	NPC258543
0.9245	High Similarity	NPC241927
0.9151	High Similarity	NPC470269
0.9151	High Similarity	NPC94529
0.9048	High Similarity	NPC310586
0.8991	High Similarity	NPC280782
0.8981	High Similarity	NPC197428
0.8972	High Similarity	NPC211224
0.8962	High Similarity	NPC475571
0.8962	High Similarity	NPC196528
0.8962	High Similarity	NPC278628
0.8962	High Similarity	NPC231530
0.8962	High Similarity	NPC181265
0.8868	High Similarity	NPC235889
0.8868	High Similarity	NPC29705
0.8857	High Similarity	NPC15396
0.8774	High Similarity	NPC140723
0.8739	High Similarity	NPC52634
0.8739	High Similarity	NPC472926
0.8716	High Similarity	NPC304495
0.8704	High Similarity	NPC44063
0.8692	High Similarity	NPC96268
0.8679	High Similarity	NPC308351
0.8679	High Similarity	NPC271266
0.8673	High Similarity	NPC472927
0.8611	High Similarity	NPC265127
0.8598	High Similarity	NPC159442
0.8584	High Similarity	NPC148458
0.8571	High Similarity	NPC962
0.8559	High Similarity	NPC43775
0.8545	High Similarity	NPC2766
0.8522	High Similarity	NPC472933
0.8519	High Similarity	NPC137657
0.8509	High Similarity	NPC239273
0.8509	High Similarity	NPC471854
0.8505	High Similarity	NPC136289
0.8505	High Similarity	NPC22388
0.8491	Intermediate Similarity	NPC15390
0.8491	Intermediate Similarity	NPC218383
0.8482	Intermediate Similarity	NPC475524
0.8482	Intermediate Similarity	NPC100267
0.8468	Intermediate Similarity	NPC129689
0.8462	Intermediate Similarity	NPC222688
0.8462	Intermediate Similarity	NPC469599
0.8448	Intermediate Similarity	NPC109973
0.844	Intermediate Similarity	NPC470267
0.844	Intermediate Similarity	NPC50535
0.8435	Intermediate Similarity	NPC311554
0.8435	Intermediate Similarity	NPC257457
0.8426	Intermediate Similarity	NPC470310
0.8421	Intermediate Similarity	NPC49492
0.8421	Intermediate Similarity	NPC266728
0.8411	Intermediate Similarity	NPC81530
0.8407	Intermediate Similarity	NPC194100
0.8407	Intermediate Similarity	NPC250109
0.8403	Intermediate Similarity	NPC15095
0.8396	Intermediate Similarity	NPC114274
0.8396	Intermediate Similarity	NPC477854
0.8393	Intermediate Similarity	NPC115303
0.8381	Intermediate Similarity	NPC200054
0.8381	Intermediate Similarity	NPC173272
0.8381	Intermediate Similarity	NPC42042
0.8381	Intermediate Similarity	NPC29410
0.8378	Intermediate Similarity	NPC286174
0.8378	Intermediate Similarity	NPC77947
0.8364	Intermediate Similarity	NPC176949
0.8364	Intermediate Similarity	NPC3316
0.8364	Intermediate Similarity	NPC251824
0.8364	Intermediate Similarity	NPC86852
0.8364	Intermediate Similarity	NPC201908
0.8364	Intermediate Similarity	NPC144854
0.8362	Intermediate Similarity	NPC473203
0.8349	Intermediate Similarity	NPC216245
0.8349	Intermediate Similarity	NPC470251
0.8349	Intermediate Similarity	NPC47281
0.8349	Intermediate Similarity	NPC2436
0.8349	Intermediate Similarity	NPC135854
0.8333	Intermediate Similarity	NPC473798
0.8319	Intermediate Similarity	NPC264634
0.8319	Intermediate Similarity	NPC473255
0.8318	Intermediate Similarity	NPC472972
0.8305	Intermediate Similarity	NPC65858
0.8302	Intermediate Similarity	NPC190554
0.8302	Intermediate Similarity	NPC108078
0.8293	Intermediate Similarity	NPC469674
0.8293	Intermediate Similarity	NPC58029
0.8291	Intermediate Similarity	NPC471406
0.8288	Intermediate Similarity	NPC154608
0.8288	Intermediate Similarity	NPC192813
0.8288	Intermediate Similarity	NPC277017
0.8286	Intermediate Similarity	NPC48330
0.8286	Intermediate Similarity	NPC98639
0.8286	Intermediate Similarity	NPC69548
0.8286	Intermediate Similarity	NPC184848
0.8273	Intermediate Similarity	NPC470309
0.8273	Intermediate Similarity	NPC28791
0.8269	Intermediate Similarity	NPC470375
0.8269	Intermediate Similarity	NPC477855
0.8269	Intermediate Similarity	NPC470376
0.8261	Intermediate Similarity	NPC96312
0.8261	Intermediate Similarity	NPC328374
0.8261	Intermediate Similarity	NPC251236
0.8261	Intermediate Similarity	NPC298278
0.8261	Intermediate Similarity	NPC40632
0.8257	Intermediate Similarity	NPC33973
0.8257	Intermediate Similarity	NPC70967
0.8257	Intermediate Similarity	NPC191892
0.8257	Intermediate Similarity	NPC87927
0.8257	Intermediate Similarity	NPC275583
0.8257	Intermediate Similarity	NPC469985
0.825	Intermediate Similarity	NPC63186
0.8246	Intermediate Similarity	NPC472929
0.8241	Intermediate Similarity	NPC289148
0.8241	Intermediate Similarity	NPC252614
0.8241	Intermediate Similarity	NPC163963
0.8241	Intermediate Similarity	NPC52899
0.8235	Intermediate Similarity	NPC135038
0.8235	Intermediate Similarity	NPC43252
0.8235	Intermediate Similarity	NPC267822
0.823	Intermediate Similarity	NPC472928
0.8224	Intermediate Similarity	NPC38296
0.8224	Intermediate Similarity	NPC477813
0.8224	Intermediate Similarity	NPC38471
0.8224	Intermediate Similarity	NPC98837
0.8224	Intermediate Similarity	NPC162459
0.8224	Intermediate Similarity	NPC471038
0.8224	Intermediate Similarity	NPC20479
0.8224	Intermediate Similarity	NPC28864
0.8211	Intermediate Similarity	NPC471855
0.8211	Intermediate Similarity	NPC34963
0.8208	Intermediate Similarity	NPC328162
0.8208	Intermediate Similarity	NPC253115
0.8208	Intermediate Similarity	NPC477853
0.8208	Intermediate Similarity	NPC305483
0.8208	Intermediate Similarity	NPC49371
0.8208	Intermediate Similarity	NPC304899
0.8208	Intermediate Similarity	NPC96859
0.8205	Intermediate Similarity	NPC475041
0.8198	Intermediate Similarity	NPC472925
0.8198	Intermediate Similarity	NPC475294
0.8198	Intermediate Similarity	NPC59530
0.8198	Intermediate Similarity	NPC165873
0.8198	Intermediate Similarity	NPC220974
0.8197	Intermediate Similarity	NPC35109
0.8197	Intermediate Similarity	NPC470880
0.819	Intermediate Similarity	NPC196485
0.819	Intermediate Similarity	NPC472934
0.819	Intermediate Similarity	NPC245972
0.819	Intermediate Similarity	NPC111015
0.8182	Intermediate Similarity	NPC470882
0.8182	Intermediate Similarity	NPC473253
0.8182	Intermediate Similarity	NPC28656
0.8182	Intermediate Similarity	NPC473265
0.8182	Intermediate Similarity	NPC477812
0.8174	Intermediate Similarity	NPC474906
0.8174	Intermediate Similarity	NPC243354
0.8174	Intermediate Similarity	NPC123117
0.8174	Intermediate Similarity	NPC18547
0.8173	Intermediate Similarity	NPC154101
0.8167	Intermediate Similarity	NPC169818
0.8165	Intermediate Similarity	NPC246736
0.8165	Intermediate Similarity	NPC286519
0.8165	Intermediate Similarity	NPC477054
0.8165	Intermediate Similarity	NPC214946
0.8165	Intermediate Similarity	NPC193934
0.8165	Intermediate Similarity	NPC473928
0.8165	Intermediate Similarity	NPC271980
0.8165	Intermediate Similarity	NPC275990
0.8165	Intermediate Similarity	NPC88203
0.8165	Intermediate Similarity	NPC304832
0.8165	Intermediate Similarity	NPC53222
0.8165	Intermediate Similarity	NPC76866
0.8165	Intermediate Similarity	NPC148628
0.8158	Intermediate Similarity	NPC152117
0.8158	Intermediate Similarity	NPC234042
0.8158	Intermediate Similarity	NPC147180
0.8158	Intermediate Similarity	NPC221144
0.8151	Intermediate Similarity	NPC269642
0.8148	Intermediate Similarity	NPC287676
0.8148	Intermediate Similarity	NPC293866
0.8148	Intermediate Similarity	NPC144956
0.8148	Intermediate Similarity	NPC83709
0.8148	Intermediate Similarity	NPC476274
0.8145	Intermediate Similarity	NPC469673
0.8142	Intermediate Similarity	NPC163314
0.8142	Intermediate Similarity	NPC76084
0.8131	Intermediate Similarity	NPC18509
0.813	Intermediate Similarity	NPC279478
0.813	Intermediate Similarity	NPC220757
0.813	Intermediate Similarity	NPC241935
0.813	Intermediate Similarity	NPC196921
0.8125	Intermediate Similarity	NPC295244

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 NPC202889 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1748
0.2-0.3	3970
0.3-0.4	2106
0.4-0.5	618
0.5-0.6	214
0.6-0.7	136
0.7-0.8	109
0.8-0.85	21
0.85-0.9	23
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8899	High Similarity	NPD6650	Approved
0.8899	High Similarity	NPD6649	Approved
0.8889	High Similarity	NPD6372	Approved
0.8889	High Similarity	NPD6373	Approved
0.8818	High Similarity	NPD8297	Approved
0.8796	High Similarity	NPD6899	Approved
0.8796	High Similarity	NPD6881	Approved
0.8785	High Similarity	NPD5739	Approved
0.8785	High Similarity	NPD7128	Approved
0.8785	High Similarity	NPD6675	Approved
0.8785	High Similarity	NPD6402	Approved
0.8727	High Similarity	NPD8130	Phase 1
0.8704	High Similarity	NPD5697	Approved
0.8649	High Similarity	NPD6882	Approved
0.8636	High Similarity	NPD7290	Approved
0.8636	High Similarity	NPD6883	Approved
0.8636	High Similarity	NPD7102	Approved
0.8624	High Similarity	NPD6011	Approved
0.8624	High Similarity	NPD7320	Approved
0.8559	High Similarity	NPD6617	Approved
0.8559	High Similarity	NPD6869	Approved
0.8559	High Similarity	NPD6847	Approved
0.8547	High Similarity	NPD7604	Phase 2
0.8545	High Similarity	NPD6013	Approved
0.8545	High Similarity	NPD6014	Approved
0.8545	High Similarity	NPD6012	Approved
0.8532	High Similarity	NPD5701	Approved
0.8448	Intermediate Similarity	NPD6319	Approved
0.844	Intermediate Similarity	NPD6008	Approved
0.8407	Intermediate Similarity	NPD4632	Approved
0.8393	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8348	Intermediate Similarity	NPD6009	Approved
0.822	Intermediate Similarity	NPD5983	Phase 2
0.8167	Intermediate Similarity	NPD7492	Approved
0.8148	Intermediate Similarity	NPD5285	Approved
0.8148	Intermediate Similarity	NPD4696	Approved
0.8148	Intermediate Similarity	NPD5286	Approved
0.8136	Intermediate Similarity	NPD6054	Approved
0.8131	Intermediate Similarity	NPD6083	Phase 2
0.8131	Intermediate Similarity	NPD4755	Approved
0.8131	Intermediate Similarity	NPD6084	Phase 2
0.812	Intermediate Similarity	NPD6335	Approved
0.8115	Intermediate Similarity	NPD7736	Approved
0.8103	Intermediate Similarity	NPD6274	Approved
0.8099	Intermediate Similarity	NPD6616	Approved
0.8099	Intermediate Similarity	NPD6336	Discontinued
0.8095	Intermediate Similarity	NPD6399	Phase 3
0.8073	Intermediate Similarity	NPD5223	Approved
0.8051	Intermediate Similarity	NPD7101	Approved
0.8051	Intermediate Similarity	NPD7100	Approved
0.8034	Intermediate Similarity	NPD6317	Approved
0.8033	Intermediate Similarity	NPD7078	Approved
0.8033	Intermediate Similarity	NPD8293	Discontinued
0.8	Intermediate Similarity	NPD5226	Approved
0.8	Intermediate Similarity	NPD4633	Approved
0.8	Intermediate Similarity	NPD6370	Approved
0.8	Intermediate Similarity	NPD5211	Phase 2
0.8	Intermediate Similarity	NPD5225	Approved
0.8	Intermediate Similarity	NPD5224	Approved
0.7983	Intermediate Similarity	NPD6059	Approved
0.7982	Intermediate Similarity	NPD4700	Approved
0.7966	Intermediate Similarity	NPD6313	Approved
0.7966	Intermediate Similarity	NPD6314	Approved
0.7928	Intermediate Similarity	NPD5175	Approved
0.7928	Intermediate Similarity	NPD5174	Approved
0.7917	Intermediate Similarity	NPD6016	Approved
0.7917	Intermediate Similarity	NPD6015	Approved
0.789	Intermediate Similarity	NPD5696	Approved
0.787	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5221	Approved
0.787	Intermediate Similarity	NPD5222	Approved
0.787	Intermediate Similarity	NPD4697	Phase 3
0.7857	Intermediate Similarity	NPD5141	Approved
0.7851	Intermediate Similarity	NPD5988	Approved
0.783	Intermediate Similarity	NPD6079	Approved
0.7826	Intermediate Similarity	NPD4634	Approved
0.781	Intermediate Similarity	NPD5328	Approved
0.7807	Intermediate Similarity	NPD4729	Approved
0.7807	Intermediate Similarity	NPD4730	Approved
0.7798	Intermediate Similarity	NPD5173	Approved
0.7797	Intermediate Similarity	NPD6868	Approved
0.7788	Intermediate Similarity	NPD4767	Approved
0.7788	Intermediate Similarity	NPD4768	Approved
0.7778	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5695	Phase 3
0.7769	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD6908	Approved
0.7769	Intermediate Similarity	NPD6909	Approved
0.7768	Intermediate Similarity	NPD4754	Approved
0.7727	Intermediate Similarity	NPD7638	Approved
0.7714	Intermediate Similarity	NPD6672	Approved
0.7714	Intermediate Similarity	NPD5737	Approved
0.7672	Intermediate Similarity	NPD5250	Approved
0.7672	Intermediate Similarity	NPD5249	Phase 3
0.7672	Intermediate Similarity	NPD5247	Approved
0.7672	Intermediate Similarity	NPD5248	Approved
0.7672	Intermediate Similarity	NPD5251	Approved
0.7658	Intermediate Similarity	NPD7640	Approved
0.7658	Intermediate Similarity	NPD7639	Approved
0.7652	Intermediate Similarity	NPD5128	Approved
0.7642	Intermediate Similarity	NPD6080	Approved
0.7642	Intermediate Similarity	NPD6904	Approved
0.7642	Intermediate Similarity	NPD8328	Phase 3
0.7642	Intermediate Similarity	NPD6673	Approved
0.7636	Intermediate Similarity	NPD7902	Approved
0.7593	Intermediate Similarity	NPD4202	Approved
0.754	Intermediate Similarity	NPD6033	Approved
0.7524	Intermediate Similarity	NPD6684	Approved
0.7524	Intermediate Similarity	NPD7334	Approved
0.7524	Intermediate Similarity	NPD3618	Phase 1
0.7524	Intermediate Similarity	NPD7521	Approved
0.7524	Intermediate Similarity	NPD6098	Approved
0.7524	Intermediate Similarity	NPD5330	Approved
0.7524	Intermediate Similarity	NPD6409	Approved
0.7524	Intermediate Similarity	NPD7146	Approved
0.7523	Intermediate Similarity	NPD7748	Approved
0.7521	Intermediate Similarity	NPD5135	Approved
0.7521	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD5169	Approved
0.75	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD4786	Approved
0.7477	Intermediate Similarity	NPD4753	Phase 2
0.7458	Intermediate Similarity	NPD5215	Approved
0.7458	Intermediate Similarity	NPD5127	Approved
0.7458	Intermediate Similarity	NPD5217	Approved
0.7458	Intermediate Similarity	NPD5216	Approved
0.7455	Intermediate Similarity	NPD4629	Approved
0.7455	Intermediate Similarity	NPD5210	Approved
0.7438	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7115	Discovery
0.7414	Intermediate Similarity	NPD6412	Phase 2
0.7383	Intermediate Similarity	NPD6903	Approved
0.7383	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7507	Approved
0.7364	Intermediate Similarity	NPD7900	Approved
0.7364	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6001	Approved
0.7339	Intermediate Similarity	NPD7515	Phase 2
0.7339	Intermediate Similarity	NPD5693	Phase 1
0.7339	Intermediate Similarity	NPD6050	Approved
0.7333	Intermediate Similarity	NPD3133	Approved
0.7333	Intermediate Similarity	NPD3665	Phase 1
0.7333	Intermediate Similarity	NPD3666	Approved
0.7308	Intermediate Similarity	NPD3667	Approved
0.7293	Intermediate Similarity	NPD6333	Approved
0.7293	Intermediate Similarity	NPD6334	Approved
0.7273	Intermediate Similarity	NPD5167	Approved
0.7264	Intermediate Similarity	NPD5329	Approved
0.725	Intermediate Similarity	NPD6053	Discontinued
0.7248	Intermediate Similarity	NPD5692	Phase 3
0.7209	Intermediate Similarity	NPD7319	Approved
0.7203	Intermediate Similarity	NPD5168	Approved
0.7182	Intermediate Similarity	NPD5284	Approved
0.7182	Intermediate Similarity	NPD5281	Approved
0.7182	Intermediate Similarity	NPD5694	Approved
0.717	Intermediate Similarity	NPD4197	Approved
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7632	Discontinued
0.7059	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5279	Phase 3
0.7037	Intermediate Similarity	NPD5690	Phase 2
0.7037	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5959	Approved
0.6981	Remote Similarity	NPD4223	Phase 3
0.6981	Remote Similarity	NPD4221	Approved
0.6975	Remote Similarity	NPD6614	Approved
0.6972	Remote Similarity	NPD3573	Approved
0.697	Remote Similarity	NPD7260	Phase 2
0.6953	Remote Similarity	NPD6067	Discontinued
0.6942	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8033	Approved
0.6917	Remote Similarity	NPD6686	Approved
0.6916	Remote Similarity	NPD4788	Approved
0.6909	Remote Similarity	NPD5208	Approved
0.6881	Remote Similarity	NPD4694	Approved
0.6881	Remote Similarity	NPD5280	Approved
0.6875	Remote Similarity	NPD6411	Approved
0.686	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3668	Phase 3
0.685	Remote Similarity	NPD8377	Approved
0.685	Remote Similarity	NPD8294	Approved
0.6842	Remote Similarity	NPD5654	Approved
0.6825	Remote Similarity	NPD7327	Approved
0.6825	Remote Similarity	NPD7328	Approved
0.6822	Remote Similarity	NPD6435	Approved
0.6803	Remote Similarity	NPD6371	Approved
0.6797	Remote Similarity	NPD8379	Approved
0.6797	Remote Similarity	NPD8335	Approved
0.6797	Remote Similarity	NPD7503	Approved
0.6797	Remote Similarity	NPD8296	Approved
0.6797	Remote Similarity	NPD8380	Approved
0.6797	Remote Similarity	NPD8378	Approved
0.6792	Remote Similarity	NPD7525	Registered
0.6792	Remote Similarity	NPD4695	Discontinued
0.6786	Remote Similarity	NPD5207	Approved
0.6774	Remote Similarity	NPD8133	Approved
0.6772	Remote Similarity	NPD7516	Approved
0.6767	Remote Similarity	NPD5956	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