NPASS Compound

Structure

CID153365 OpenBabel06191715522D 44 48 0 0 1 0 0 0 0 0999 V2000 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0263 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 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 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -5.0000 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 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 -7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -7.7942 -4.5000 0.0000 C 0 0 0 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 -4.3301 -0.5000 0.0000 C 0 0 0 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -4.5000 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 3.4641 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 N 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 30 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 6 39 1 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 10 2 0 0 0 0 8 17 1 0 0 0 0 9 19 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 30 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 18 2 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 16 26 1 0 0 0 0 17 21 1 0 0 0 0 17 23 2 0 0 0 0 18 40 1 0 0 0 0 19 43 1 0 0 0 0 20 21 2 0 0 0 0 20 27 1 0 0 0 0 20 33 1 0 0 0 0 21 34 1 0 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 22 35 1 6 0 0 0 23 41 1 0 0 0 0 24 25 1 0 0 0 0 24 42 1 6 0 0 0 25 31 1 0 0 0 0 25 39 1 1 0 0 0 26 33 1 0 0 0 0 26 36 2 0 0 0 0 27 37 2 0 0 0 0 27 41 1 0 0 0 0 28 40 1 1 0 0 0 28 44 1 0 0 0 0 29 32 2 0 0 0 0 29 38 1 0 0 0 0 29 42 1 0 0 0 0 30 43 1 0 0 0 0 31 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.23
Volume:	594.271
LogP:	3.888
LogD:	2.652
LogS:	-4.733
# Rotatable Bonds:	8
TPSA:	189.01
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	4.441
Fsp3:	0.452
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.38
MDCK Permeability:	1.7648349967203103e-05
Pgp-inhibitor:	0.564
Pgp-substrate:	0.948
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	91.12733459472656%
Volume Distribution (VD):	0.945
Pgp-substrate:	5.030697822570801%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.162
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.219
CYP2D6-inhibitor:	0.242
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.165
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	2.577
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.18
Rat Oral Acute Toxicity:	0.593
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.089
Carcinogencity:	0.412
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.003

Download Data

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

Natural Product: NPC153365

Natural Product ID:	NPC153365
*Common Name:**	Coumabiocin C
IUPAC Name:	[(3R,4S,5R,6R)-6-[3-[(2,2-dimethyl-3,4-dihydrochromene-6-carbonyl)amino]-4-hydroxy-8-methyl-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] carbamate
Synonyms:	Coumabiocin C
Standard InCHIKey:	XHPKFSICBQUAKE-BOFKSZNZSA-N
Standard InCHI:	InChI=1S/C31H36N2O11/c1-14-18(40-28-22(35)24(42-29(32)38)25(39-6)31(4,5)44-28)10-8-17-21(34)20(27(37)41-23(14)17)33-26(36)16-7-9-19-15(13-16)11-12-30(2,3)43-19/h7-10,13,22,24-25,28,34-35H,11-12H2,1-6H3,(H2,32,38)(H,33,36)/t22-,24+,25-,28-/m1/s1
SMILES:	Cc1c(ccc2c(c(c(=O)oc12)NC(=O)c1ccc2c(CCC(C)(C)O2)c1)O)O[C@H]1[C@@H]([C@@H]([C@H](C(C)(C)O1)OC)OC(=N)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097289
PubChem CID:	54734319
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0001743] Coumarin glycosides

*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
NPO40222	Streptomyces sp. L-4-4	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20384319]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	15.0	mm	PMID[543677]
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	10.0	mm	PMID[543677]

☑ 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 NPC153365 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	370
0.1-0.2	1817
0.2-0.3	5917
0.3-0.4	11090
0.4-0.5	6897
0.5-0.6	9926
0.6-0.7	6247
0.7-0.8	420
0.8-0.85	1
0.85-0.9	4
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC257266
0.9839	High Similarity	NPC257728
0.8263	Intermediate Similarity	NPC314656
0.8115	Intermediate Similarity	NPC314025
0.8073	Intermediate Similarity	NPC314213
0.8031	Intermediate Similarity	NPC315913
0.7842	Intermediate Similarity	NPC257566
0.7842	Intermediate Similarity	NPC124155
0.7824	Intermediate Similarity	NPC76047
0.7789	Intermediate Similarity	NPC44947
0.7739	Intermediate Similarity	NPC469437
0.7737	Intermediate Similarity	NPC47923
0.7737	Intermediate Similarity	NPC303913
0.7737	Intermediate Similarity	NPC101636
0.7736	Intermediate Similarity	NPC478048
0.7725	Intermediate Similarity	NPC43761
0.77	Intermediate Similarity	NPC180210
0.77	Intermediate Similarity	NPC314914
0.77	Intermediate Similarity	NPC321226
0.77	Intermediate Similarity	NPC328856
0.77	Intermediate Similarity	NPC478046
0.77	Intermediate Similarity	NPC478047
0.7696	Intermediate Similarity	NPC190450
0.7696	Intermediate Similarity	NPC298171
0.7684	Intermediate Similarity	NPC472320
0.768	Intermediate Similarity	NPC5319
0.7676	Intermediate Similarity	NPC107197
0.7664	Intermediate Similarity	NPC316368
0.7664	Intermediate Similarity	NPC284236
0.7656	Intermediate Similarity	NPC183672
0.7632	Intermediate Similarity	NPC73511
0.7632	Intermediate Similarity	NPC473634
0.7632	Intermediate Similarity	NPC138811
0.7632	Intermediate Similarity	NPC22062
0.763	Intermediate Similarity	NPC92235
0.7619	Intermediate Similarity	NPC473657
0.7619	Intermediate Similarity	NPC295613
0.7619	Intermediate Similarity	NPC45165
0.7614	Intermediate Similarity	NPC63105
0.7604	Intermediate Similarity	NPC472876
0.7604	Intermediate Similarity	NPC259834
0.7604	Intermediate Similarity	NPC131745
0.7593	Intermediate Similarity	NPC170101
0.7592	Intermediate Similarity	NPC473623
0.7592	Intermediate Similarity	NPC271270
0.7592	Intermediate Similarity	NPC142860
0.7592	Intermediate Similarity	NPC97285
0.7592	Intermediate Similarity	NPC246469
0.7591	Intermediate Similarity	NPC315914
0.7579	Intermediate Similarity	NPC197896
0.7579	Intermediate Similarity	NPC44931
0.7579	Intermediate Similarity	NPC313163
0.7579	Intermediate Similarity	NPC156457
0.7579	Intermediate Similarity	NPC43638
0.7579	Intermediate Similarity	NPC161749
0.7579	Intermediate Similarity	NPC65003
0.7579	Intermediate Similarity	NPC129827
0.7579	Intermediate Similarity	NPC473512
0.7579	Intermediate Similarity	NPC258035
0.7579	Intermediate Similarity	NPC23817
0.7577	Intermediate Similarity	NPC68592
0.7577	Intermediate Similarity	NPC64425
0.7577	Intermediate Similarity	NPC262222
0.7577	Intermediate Similarity	NPC298666
0.7565	Intermediate Similarity	NPC179198
0.7565	Intermediate Similarity	NPC66087
0.7565	Intermediate Similarity	NPC278419
0.7563	Intermediate Similarity	NPC208668
0.7563	Intermediate Similarity	NPC163165
0.7562	Intermediate Similarity	NPC106700
0.7561	Intermediate Similarity	NPC83019
0.7552	Intermediate Similarity	NPC477628
0.7552	Intermediate Similarity	NPC195685
0.7552	Intermediate Similarity	NPC477629
0.7552	Intermediate Similarity	NPC270675
0.7552	Intermediate Similarity	NPC472994
0.7552	Intermediate Similarity	NPC210961
0.7551	Intermediate Similarity	NPC150767
0.7551	Intermediate Similarity	NPC209550
0.7551	Intermediate Similarity	NPC138990
0.7551	Intermediate Similarity	NPC210808
0.7551	Intermediate Similarity	NPC175429
0.7551	Intermediate Similarity	NPC199079
0.7551	Intermediate Similarity	NPC78734
0.7551	Intermediate Similarity	NPC277532
0.755	Intermediate Similarity	NPC477860
0.755	Intermediate Similarity	NPC475161
0.7538	Intermediate Similarity	NPC249977
0.7531	Intermediate Similarity	NPC172355
0.7526	Intermediate Similarity	NPC475979
0.7526	Intermediate Similarity	NPC139060
0.7526	Intermediate Similarity	NPC170475
0.7526	Intermediate Similarity	NPC127406
0.7526	Intermediate Similarity	NPC206378
0.7526	Intermediate Similarity	NPC294722
0.7514	Intermediate Similarity	NPC87950
0.7514	Intermediate Similarity	NPC471764
0.7513	Intermediate Similarity	NPC475382
0.7513	Intermediate Similarity	NPC288152
0.7513	Intermediate Similarity	NPC256760
0.7513	Intermediate Similarity	NPC240306
0.7513	Intermediate Similarity	NPC257011
0.7513	Intermediate Similarity	NPC137871
0.7513	Intermediate Similarity	NPC474522
0.7513	Intermediate Similarity	NPC9002
0.7512	Intermediate Similarity	NPC204580
0.75	Intermediate Similarity	NPC200708
0.75	Intermediate Similarity	NPC271479
0.75	Intermediate Similarity	NPC245059
0.75	Intermediate Similarity	NPC187379
0.75	Intermediate Similarity	NPC84494
0.7489	Intermediate Similarity	NPC252156
0.7488	Intermediate Similarity	NPC282636
0.7488	Intermediate Similarity	NPC294863
0.7487	Intermediate Similarity	NPC473278
0.7487	Intermediate Similarity	NPC103116
0.7487	Intermediate Similarity	NPC100818
0.7487	Intermediate Similarity	NPC70441
0.7487	Intermediate Similarity	NPC325176
0.7487	Intermediate Similarity	NPC260504
0.7487	Intermediate Similarity	NPC89809
0.7487	Intermediate Similarity	NPC79736
0.7487	Intermediate Similarity	NPC67629
0.7477	Intermediate Similarity	NPC315253
0.7475	Intermediate Similarity	NPC75574
0.7475	Intermediate Similarity	NPC213052
0.7475	Intermediate Similarity	NPC309692
0.7475	Intermediate Similarity	NPC25724
0.7474	Intermediate Similarity	NPC72649
0.7474	Intermediate Similarity	NPC470604
0.7474	Intermediate Similarity	NPC99233
0.7474	Intermediate Similarity	NPC95090
0.7474	Intermediate Similarity	NPC473644
0.7474	Intermediate Similarity	NPC97052
0.7474	Intermediate Similarity	NPC26195
0.7474	Intermediate Similarity	NPC470603
0.7474	Intermediate Similarity	NPC470605
0.7474	Intermediate Similarity	NPC80068
0.7474	Intermediate Similarity	NPC169248
0.7474	Intermediate Similarity	NPC27408
0.7474	Intermediate Similarity	NPC39351
0.7474	Intermediate Similarity	NPC311850
0.7474	Intermediate Similarity	NPC121290
0.7474	Intermediate Similarity	NPC121703
0.7474	Intermediate Similarity	NPC477958
0.7463	Intermediate Similarity	NPC470448
0.7463	Intermediate Similarity	NPC470452
0.7463	Intermediate Similarity	NPC164047
0.7463	Intermediate Similarity	NPC53680
0.7463	Intermediate Similarity	NPC208797
0.7463	Intermediate Similarity	NPC470453
0.7462	Intermediate Similarity	NPC188815
0.7462	Intermediate Similarity	NPC470712
0.7462	Intermediate Similarity	NPC164704
0.7462	Intermediate Similarity	NPC51326
0.7462	Intermediate Similarity	NPC218488
0.7462	Intermediate Similarity	NPC231194
0.7461	Intermediate Similarity	NPC48093
0.7461	Intermediate Similarity	NPC476215
0.7461	Intermediate Similarity	NPC246943
0.7461	Intermediate Similarity	NPC159579
0.7461	Intermediate Similarity	NPC139320
0.7461	Intermediate Similarity	NPC259957
0.7461	Intermediate Similarity	NPC116458
0.7461	Intermediate Similarity	NPC253788
0.7461	Intermediate Similarity	NPC265885
0.7461	Intermediate Similarity	NPC163242
0.7461	Intermediate Similarity	NPC249281
0.7461	Intermediate Similarity	NPC216496
0.7461	Intermediate Similarity	NPC276377
0.7461	Intermediate Similarity	NPC173582
0.7461	Intermediate Similarity	NPC473438
0.7461	Intermediate Similarity	NPC129217
0.7461	Intermediate Similarity	NPC85707
0.7461	Intermediate Similarity	NPC224530
0.7461	Intermediate Similarity	NPC215710
0.7461	Intermediate Similarity	NPC181465
0.745	Intermediate Similarity	NPC267549
0.7448	Intermediate Similarity	NPC470607
0.7448	Intermediate Similarity	NPC308265
0.7437	Intermediate Similarity	NPC169645
0.7437	Intermediate Similarity	NPC294629
0.7437	Intermediate Similarity	NPC84482
0.7436	Intermediate Similarity	NPC19240
0.7436	Intermediate Similarity	NPC129264
0.7436	Intermediate Similarity	NPC284277
0.7436	Intermediate Similarity	NPC475497
0.7436	Intermediate Similarity	NPC135358
0.7436	Intermediate Similarity	NPC7752
0.7436	Intermediate Similarity	NPC475366
0.7436	Intermediate Similarity	NPC287889
0.7436	Intermediate Similarity	NPC72016
0.7436	Intermediate Similarity	NPC205824
0.7436	Intermediate Similarity	NPC85751
0.7436	Intermediate Similarity	NPC99216
0.7435	Intermediate Similarity	NPC17521
0.7424	Intermediate Similarity	NPC221288
0.7424	Intermediate Similarity	NPC217822
0.7424	Intermediate Similarity	NPC470715
0.7424	Intermediate Similarity	NPC475155

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 NPC153365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	632
0.2-0.3	1215
0.3-0.4	2151
0.4-0.5	2813
0.5-0.6	1687
0.6-0.7	381
0.7-0.8	20
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9892	High Similarity	NPD7583	Approved
0.9839	High Similarity	NPD7585	Approved
0.9267	High Similarity	NPD7584	Approved
0.768	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7783	Phase 2
0.744	Intermediate Similarity	NPD7811	Phase 3
0.744	Intermediate Similarity	NPD7810	Phase 3
0.7436	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7054	Approved
0.7387	Intermediate Similarity	NPD5192	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7074	Phase 3
0.7374	Intermediate Similarity	NPD7472	Approved
0.736	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7701	Phase 2
0.7321	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7075	Discontinued
0.73	Intermediate Similarity	NPD7251	Discontinued
0.729	Intermediate Similarity	NPD8151	Discontinued
0.7264	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7808	Phase 3
0.7263	Intermediate Similarity	NPD4380	Phase 2
0.725	Intermediate Similarity	NPD6797	Phase 2
0.724	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8059	Phase 3
0.7217	Intermediate Similarity	NPD7696	Phase 3
0.7217	Intermediate Similarity	NPD7698	Approved
0.7217	Intermediate Similarity	NPD7697	Approved
0.7214	Intermediate Similarity	NPD7039	Approved
0.7214	Intermediate Similarity	NPD7038	Approved
0.7208	Intermediate Similarity	NPD5242	Approved
0.7202	Intermediate Similarity	NPD7930	Approved
0.7191	Intermediate Similarity	NPD8153	Approved
0.7191	Intermediate Similarity	NPD8152	Approved
0.7188	Intermediate Similarity	NPD6801	Discontinued
0.7183	Intermediate Similarity	NPD8319	Approved
0.7183	Intermediate Similarity	NPD8320	Phase 1
0.717	Intermediate Similarity	NPD6823	Phase 2
0.7164	Intermediate Similarity	NPD3823	Discontinued
0.7156	Intermediate Similarity	NPD6778	Approved
0.7156	Intermediate Similarity	NPD6781	Approved
0.7156	Intermediate Similarity	NPD6782	Approved
0.7156	Intermediate Similarity	NPD6780	Approved
0.7156	Intermediate Similarity	NPD6779	Approved
0.7156	Intermediate Similarity	NPD6777	Approved
0.7156	Intermediate Similarity	NPD6776	Approved
0.715	Intermediate Similarity	NPD7999	Approved
0.715	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD7801	Approved
0.7136	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6559	Discontinued
0.7116	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7870	Phase 2
0.7103	Intermediate Similarity	NPD7871	Phase 2
0.71	Intermediate Similarity	NPD3818	Discontinued
0.7097	Intermediate Similarity	NPD7874	Approved
0.7097	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5005	Approved
0.7089	Intermediate Similarity	NPD5006	Approved
0.7085	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4363	Phase 3
0.7081	Intermediate Similarity	NPD4360	Phase 2
0.7077	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5844	Phase 1
0.7056	Intermediate Similarity	NPD7435	Discontinued
0.7047	Intermediate Similarity	NPD7411	Suspended
0.7028	Intermediate Similarity	NPD8285	Discontinued
0.7028	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6625	Approved
0.6986	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4420	Approved
0.6981	Remote Similarity	NPD7699	Phase 2
0.6981	Remote Similarity	NPD7700	Phase 2
0.6974	Remote Similarity	NPD7819	Suspended
0.695	Remote Similarity	NPD2388	Discontinued
0.6931	Remote Similarity	NPD7177	Discontinued
0.6919	Remote Similarity	NPD6534	Approved
0.6919	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6535	Approved
0.6916	Remote Similarity	NPD5457	Discontinued
0.6915	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6166	Phase 2
0.6912	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8404	Phase 2
0.6903	Remote Similarity	NPD6997	Phase 2
0.6893	Remote Similarity	NPD8313	Approved
0.6893	Remote Similarity	NPD8312	Approved
0.689	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4361	Phase 2
0.6887	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2904	Discontinued
0.6878	Remote Similarity	NPD6104	Discontinued
0.6875	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6213	Phase 3
0.6872	Remote Similarity	NPD4466	Phase 1
0.6872	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6212	Phase 3
0.6869	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6853	Approved
0.686	Remote Similarity	NPD6851	Approved
0.6856	Remote Similarity	NPD8469	Approved
0.6856	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1898	Discontinued
0.6839	Remote Similarity	NPD5403	Approved
0.6832	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3819	Phase 2
0.6823	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7608	Discontinued
0.6806	Remote Similarity	NPD7476	Discontinued
0.6803	Remote Similarity	NPD8461	Discontinued
0.6791	Remote Similarity	NPD7565	Approved
0.6789	Remote Similarity	NPD4628	Phase 3
0.6786	Remote Similarity	NPD5889	Approved
0.6786	Remote Similarity	NPD5890	Approved
0.6776	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6799	Approved
0.6769	Remote Similarity	NPD7458	Discontinued
0.6768	Remote Similarity	NPD3817	Phase 2
0.6768	Remote Similarity	NPD5402	Approved
0.6766	Remote Similarity	NPD7048	Phase 3
0.6765	Remote Similarity	NPD7228	Approved
0.6762	Remote Similarity	NPD7693	Approved
0.6751	Remote Similarity	NPD1934	Approved
0.6737	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7447	Phase 1
0.6736	Remote Similarity	NPD5401	Approved
0.6735	Remote Similarity	NPD6585	Discontinued
0.6734	Remote Similarity	NPD7768	Phase 2
0.6728	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7827	Phase 1
0.6719	Remote Similarity	NPD6666	Approved
0.6719	Remote Similarity	NPD6667	Approved
0.6718	Remote Similarity	NPD1653	Approved
0.6717	Remote Similarity	NPD1465	Phase 2
0.6716	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5677	Discontinued
0.6715	Remote Similarity	NPD7685	Pre-registration
0.6714	Remote Similarity	NPD6181	Discontinued
0.6714	Remote Similarity	NPD8150	Discontinued
0.6713	Remote Similarity	NPD6874	Approved
0.6711	Remote Similarity	NPD7047	Phase 3
0.6711	Remote Similarity	NPD8366	Approved
0.6702	Remote Similarity	NPD3750	Approved
0.6701	Remote Similarity	NPD6677	Suspended
0.6701	Remote Similarity	NPD6072	Discontinued
0.6695	Remote Similarity	NPD8067	Phase 3
0.6684	Remote Similarity	NPD7213	Phase 3
0.6684	Remote Similarity	NPD1549	Phase 2
0.6684	Remote Similarity	NPD7212	Phase 2
0.6683	Remote Similarity	NPD7318	Phase 3
0.6683	Remote Similarity	NPD7549	Discontinued
0.6683	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5353	Approved
0.6683	Remote Similarity	NPD6959	Discontinued
0.6682	Remote Similarity	NPD7256	Discontinued
0.6682	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD4433	Discontinued
0.6667	Remote Similarity	NPD8491	Approved
0.6667	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD6297	Approved
0.6652	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6042	Phase 2
0.665	Remote Similarity	NPD42	Phase 2
0.665	Remote Similarity	NPD6599	Discontinued
0.6649	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD8149	Discontinued
0.6636	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5494	Approved
0.6634	Remote Similarity	NPD4666	Phase 3
0.6634	Remote Similarity	NPD3366	Approved
0.6632	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD5124	Phase 1
0.6631	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6863	Phase 2
0.6621	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD8162	Phase 2
0.6619	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8031	Discontinued

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