NPASS Compound

Structure

CID314213 OpenBabel06191716122D 45 49 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3627 5.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3627 4.9487 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 -7.7942 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 -8.6603 2.0000 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 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0021 4.4781 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 -6.9282 2.0000 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 -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 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9967 4.5827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -9.4967 5.4487 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 -6.0622 0.5000 0.0000 N 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 0.8660 -2.5000 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 -6.0622 -1.5000 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 -8.9967 6.3147 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 -9.4034 3.6691 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 -4.3301 -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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 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 40 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 13 23 1 0 0 0 0 14 26 1 0 0 0 0 15 18 2 0 0 0 0 16 21 1 0 0 0 0 16 23 2 0 0 0 0 17 42 1 0 0 0 0 18 41 1 0 0 0 0 19 30 1 0 0 0 0 19 41 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 1 0 0 0 23 43 1 0 0 0 0 24 25 1 0 0 0 0 24 44 1 1 0 0 0 25 31 1 0 0 0 0 25 40 1 6 0 0 0 26 33 2 3 0 0 0 26 36 1 0 0 0 0 27 37 2 0 0 0 0 27 43 1 0 0 0 0 28 42 1 6 0 0 0 28 45 1 0 0 0 0 29 32 2 0 0 0 0 29 38 1 0 0 0 0 29 44 1 0 0 0 0 30 39 1 0 0 0 0 31 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	628.23
Volume:	603.061
LogP:	2.853
LogD:	1.825
LogS:	-4.499
# Rotatable Bonds:	9
TPSA:	209.24
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.256
Synthetic Accessibility Score:	4.667
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:	-5.783
MDCK Permeability:	2.5594034013920464e-05
Pgp-inhibitor:	0.141
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	82.5601577758789%
Volume Distribution (VD):	0.955
Pgp-substrate:	8.061965942382812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.127
CYP2C9-inhibitor:	0.101
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.177
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	2.947
Half-life (T1/2):	0.229

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.951
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.281
Rat Oral Acute Toxicity:	0.749
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.072
Carcinogencity:	0.271
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.002

Download Data

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

Natural Product: NPC314213

Natural Product ID:	NPC314213
*Common Name:**	Coumabiocin A
IUPAC Name:	[(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-carbonyl]amino]-8-methyl-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] carbamate
Synonyms:
Standard InCHIKey:	QABCYUIASODPGV-AMAVTPQFSA-N
Standard InCHI:	InChI=1S/C31H36N2O12/c1-13-17(42-28-22(35)24(44-29(32)38)25(40-6)31(4,5)45-28)10-8-16-21(34)20(27(37)43-23(13)16)33-26(36)14-7-9-18-15(11-14)12-19(41-18)30(2,3)39/h7-11,19,22,24-25,28,34-35,39H,12H2,1-6H3,(H2,32,38)(H,33,36)/t19?,22-,24+,25-,28-/m1/s1
SMILES:	CO[C@@H]1[C@@H](OC(=N)O)[C@@H](O)[C@@H](OC1(C)C)Oc1ccc2c(c1C)oc(=O)c(c2O)N=C(c1ccc2c(c1)CC(O2)C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097287
PubChem CID:	54734317
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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	13.0	mm	PMID[568407]

☑ 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 NPC314213 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	333
0.1-0.2	1616
0.2-0.3	4822
0.3-0.4	10883
0.4-0.5	7273
0.5-0.6	9437
0.6-0.7	7029
0.7-0.8	1291
0.8-0.85	0
0.85-0.9	5
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC315913
0.9816	High Similarity	NPC314025
0.9756	High Similarity	NPC314656
0.8528	High Similarity	NPC169510
0.8466	Intermediate Similarity	NPC296377
0.8354	Intermediate Similarity	NPC87950
0.8354	Intermediate Similarity	NPC471764
0.8344	Intermediate Similarity	NPC85624
0.8344	Intermediate Similarity	NPC226722
0.8158	Intermediate Similarity	NPC257266
0.8115	Intermediate Similarity	NPC257728
0.8107	Intermediate Similarity	NPC53587
0.8107	Intermediate Similarity	NPC470264
0.8107	Intermediate Similarity	NPC176186
0.8107	Intermediate Similarity	NPC169404
0.8098	Intermediate Similarity	NPC215512
0.8098	Intermediate Similarity	NPC476442
0.8073	Intermediate Similarity	NPC153365
0.8072	Intermediate Similarity	NPC74320
0.8072	Intermediate Similarity	NPC107120
0.8061	Intermediate Similarity	NPC471824
0.8059	Intermediate Similarity	NPC150442
0.8012	Intermediate Similarity	NPC469701
0.8	Intermediate Similarity	NPC302610
0.7988	Intermediate Similarity	NPC195357
0.7988	Intermediate Similarity	NPC152771
0.7975	Intermediate Similarity	NPC279573
0.7939	Intermediate Similarity	NPC472353
0.7927	Intermediate Similarity	NPC312881
0.7914	Intermediate Similarity	NPC184861
0.7914	Intermediate Similarity	NPC281014
0.7914	Intermediate Similarity	NPC212124
0.7914	Intermediate Similarity	NPC225106
0.7914	Intermediate Similarity	NPC294456
0.7914	Intermediate Similarity	NPC153818
0.7914	Intermediate Similarity	NPC232246
0.7895	Intermediate Similarity	NPC476352
0.7895	Intermediate Similarity	NPC215060
0.7892	Intermediate Similarity	NPC116922
0.7882	Intermediate Similarity	NPC100818
0.7882	Intermediate Similarity	NPC107197
0.7879	Intermediate Similarity	NPC5155
0.7879	Intermediate Similarity	NPC287286
0.7879	Intermediate Similarity	NPC108674
0.787	Intermediate Similarity	NPC93924
0.7866	Intermediate Similarity	NPC151946
0.7866	Intermediate Similarity	NPC211110
0.7853	Intermediate Similarity	NPC103409
0.7853	Intermediate Similarity	NPC26954
0.7853	Intermediate Similarity	NPC38099
0.7853	Intermediate Similarity	NPC78746
0.7853	Intermediate Similarity	NPC224543
0.7853	Intermediate Similarity	NPC188380
0.7844	Intermediate Similarity	NPC177597
0.7844	Intermediate Similarity	NPC313414
0.7844	Intermediate Similarity	NPC225445
0.7831	Intermediate Similarity	NPC5253
0.7831	Intermediate Similarity	NPC139976
0.7831	Intermediate Similarity	NPC49542
0.7831	Intermediate Similarity	NPC128337
0.7831	Intermediate Similarity	NPC230718
0.7831	Intermediate Similarity	NPC84207
0.7829	Intermediate Similarity	NPC173726
0.7829	Intermediate Similarity	NPC241600
0.7811	Intermediate Similarity	NPC469700
0.7805	Intermediate Similarity	NPC87777
0.7805	Intermediate Similarity	NPC155963
0.7805	Intermediate Similarity	NPC262328
0.7798	Intermediate Similarity	NPC108994
0.7798	Intermediate Similarity	NPC106126
0.7791	Intermediate Similarity	NPC33986
0.7791	Intermediate Similarity	NPC472525
0.7778	Intermediate Similarity	NPC103116
0.7765	Intermediate Similarity	NPC270751
0.7758	Intermediate Similarity	NPC144512
0.7758	Intermediate Similarity	NPC137262
0.7758	Intermediate Similarity	NPC278600
0.7758	Intermediate Similarity	NPC35501
0.7758	Intermediate Similarity	NPC47040
0.7758	Intermediate Similarity	NPC37428
0.7744	Intermediate Similarity	NPC20829
0.7744	Intermediate Similarity	NPC262585
0.7744	Intermediate Similarity	NPC18189
0.7744	Intermediate Similarity	NPC166180
0.773	Intermediate Similarity	NPC98179
0.773	Intermediate Similarity	NPC253574
0.773	Intermediate Similarity	NPC180716
0.773	Intermediate Similarity	NPC62366
0.773	Intermediate Similarity	NPC131950
0.773	Intermediate Similarity	NPC326600
0.773	Intermediate Similarity	NPC224475
0.773	Intermediate Similarity	NPC213173
0.773	Intermediate Similarity	NPC50896
0.773	Intermediate Similarity	NPC204353
0.7727	Intermediate Similarity	NPC478269
0.7719	Intermediate Similarity	NPC106138
0.7706	Intermediate Similarity	NPC97240
0.7706	Intermediate Similarity	NPC52740
0.7697	Intermediate Similarity	NPC124149
0.7688	Intermediate Similarity	NPC59692
0.7688	Intermediate Similarity	NPC10221
0.7688	Intermediate Similarity	NPC187028
0.7688	Intermediate Similarity	NPC18249
0.7688	Intermediate Similarity	NPC140915
0.7688	Intermediate Similarity	NPC305700
0.7688	Intermediate Similarity	NPC197741
0.7674	Intermediate Similarity	NPC472710
0.7674	Intermediate Similarity	NPC114740
0.7674	Intermediate Similarity	NPC472709
0.7669	Intermediate Similarity	NPC31849
0.7669	Intermediate Similarity	NPC133956
0.7669	Intermediate Similarity	NPC296624
0.7669	Intermediate Similarity	NPC318400
0.7669	Intermediate Similarity	NPC471910
0.7669	Intermediate Similarity	NPC207002
0.7669	Intermediate Similarity	NPC215037
0.7669	Intermediate Similarity	NPC167111
0.7669	Intermediate Similarity	NPC469449
0.7665	Intermediate Similarity	NPC210192
0.7661	Intermediate Similarity	NPC476348
0.7661	Intermediate Similarity	NPC96294
0.7661	Intermediate Similarity	NPC187398
0.7661	Intermediate Similarity	NPC220282
0.7654	Intermediate Similarity	NPC124155
0.7654	Intermediate Similarity	NPC183672
0.7654	Intermediate Similarity	NPC257566
0.7651	Intermediate Similarity	NPC475836
0.7644	Intermediate Similarity	NPC469699
0.764	Intermediate Similarity	NPC470936
0.764	Intermediate Similarity	NPC478267
0.7637	Intermediate Similarity	NPC76047
0.763	Intermediate Similarity	NPC213197
0.7627	Intermediate Similarity	NPC43761
0.7627	Intermediate Similarity	NPC470607
0.7624	Intermediate Similarity	NPC208818
0.7622	Intermediate Similarity	NPC18804
0.7622	Intermediate Similarity	NPC307412
0.7622	Intermediate Similarity	NPC124085
0.7622	Intermediate Similarity	NPC195343
0.7622	Intermediate Similarity	NPC267412
0.7622	Intermediate Similarity	NPC55149
0.7622	Intermediate Similarity	NPC260265
0.7622	Intermediate Similarity	NPC319859
0.7622	Intermediate Similarity	NPC287182
0.7622	Intermediate Similarity	NPC117048
0.7622	Intermediate Similarity	NPC47163
0.7622	Intermediate Similarity	NPC84894
0.7622	Intermediate Similarity	NPC198381
0.7622	Intermediate Similarity	NPC74655
0.7622	Intermediate Similarity	NPC164269
0.7622	Intermediate Similarity	NPC127888
0.7622	Intermediate Similarity	NPC100986
0.7622	Intermediate Similarity	NPC166672
0.7619	Intermediate Similarity	NPC145319
0.7619	Intermediate Similarity	NPC63628
0.7619	Intermediate Similarity	NPC178466
0.7614	Intermediate Similarity	NPC17521
0.7614	Intermediate Similarity	NPC228357
0.7614	Intermediate Similarity	NPC284810
0.7611	Intermediate Similarity	NPC72016
0.7607	Intermediate Similarity	NPC14248
0.7602	Intermediate Similarity	NPC476347
0.7602	Intermediate Similarity	NPC15577
0.7602	Intermediate Similarity	NPC41844
0.7602	Intermediate Similarity	NPC175275
0.76	Intermediate Similarity	NPC8712
0.7598	Intermediate Similarity	NPC44947
0.7598	Intermediate Similarity	NPC131745
0.7594	Intermediate Similarity	NPC475919
0.7594	Intermediate Similarity	NPC474661
0.7593	Intermediate Similarity	NPC474491
0.7588	Intermediate Similarity	NPC43508
0.7588	Intermediate Similarity	NPC476301
0.7588	Intermediate Similarity	NPC475096
0.7586	Intermediate Similarity	NPC476452
0.7576	Intermediate Similarity	NPC471625
0.7576	Intermediate Similarity	NPC86892
0.7576	Intermediate Similarity	NPC281241
0.7576	Intermediate Similarity	NPC471909
0.7576	Intermediate Similarity	NPC79957
0.7576	Intermediate Similarity	NPC472424
0.7572	Intermediate Similarity	NPC294522
0.7572	Intermediate Similarity	NPC21184
0.7572	Intermediate Similarity	NPC205727
0.7572	Intermediate Similarity	NPC120426
0.7571	Intermediate Similarity	NPC122809
0.7571	Intermediate Similarity	NPC470606
0.7569	Intermediate Similarity	NPC475621
0.7568	Intermediate Similarity	NPC325176
0.7561	Intermediate Similarity	NPC141822
0.7561	Intermediate Similarity	NPC469965
0.7561	Intermediate Similarity	NPC241165
0.7561	Intermediate Similarity	NPC1220
0.7561	Intermediate Similarity	NPC205797
0.7561	Intermediate Similarity	NPC92805
0.7561	Intermediate Similarity	NPC7526
0.7561	Intermediate Similarity	NPC85435
0.7561	Intermediate Similarity	NPC222036
0.7561	Intermediate Similarity	NPC291551
0.7561	Intermediate Similarity	NPC142563

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 NPC314213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	637
0.2-0.3	1142
0.3-0.4	2188
0.4-0.5	2845
0.5-0.6	1683
0.6-0.7	379
0.7-0.8	46
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8158	Intermediate Similarity	NPD7583	Approved
0.8115	Intermediate Similarity	NPD7585	Approved
0.7791	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7584	Approved
0.7561	Intermediate Similarity	NPD5124	Phase 1
0.7561	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD1653	Approved
0.7486	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6559	Discontinued
0.735	Intermediate Similarity	NPD8151	Discontinued
0.731	Intermediate Similarity	NPD6823	Phase 2
0.7303	Intermediate Similarity	NPD8455	Phase 2
0.7251	Intermediate Similarity	NPD1652	Phase 2
0.7204	Intermediate Similarity	NPD7054	Approved
0.7192	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7783	Phase 2
0.7191	Intermediate Similarity	NPD6072	Discontinued
0.7182	Intermediate Similarity	NPD7075	Discontinued
0.7166	Intermediate Similarity	NPD7074	Phase 3
0.7166	Intermediate Similarity	NPD7472	Approved
0.7157	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7228	Approved
0.7151	Intermediate Similarity	NPD3818	Discontinued
0.7135	Intermediate Similarity	NPD4380	Phase 2
0.7135	Intermediate Similarity	NPD7266	Discontinued
0.7111	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7801	Approved
0.7093	Intermediate Similarity	NPD2424	Discontinued
0.709	Intermediate Similarity	NPD7251	Discontinued
0.7079	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2415	Discontinued
0.7066	Intermediate Similarity	NPD1048	Approved
0.7066	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD37	Approved
0.7056	Intermediate Similarity	NPD6801	Discontinued
0.7053	Intermediate Similarity	NPD7808	Phase 3
0.7053	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6842	Approved
0.7047	Intermediate Similarity	NPD6843	Phase 3
0.7047	Intermediate Similarity	NPD6841	Approved
0.7045	Intermediate Similarity	NPD7447	Phase 1
0.7037	Intermediate Similarity	NPD6797	Phase 2
0.7037	Intermediate Similarity	NPD1091	Approved
0.7037	Intermediate Similarity	NPD7007	Discovery
0.7033	Intermediate Similarity	NPD4965	Approved
0.7033	Intermediate Similarity	NPD4966	Approved
0.7033	Intermediate Similarity	NPD4967	Phase 2
0.7029	Intermediate Similarity	NPD5058	Phase 3
0.6989	Remote Similarity	NPD7213	Phase 3
0.6989	Remote Similarity	NPD7212	Phase 2
0.6982	Remote Similarity	NPD1613	Approved
0.6982	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7874	Approved
0.6976	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7199	Phase 2
0.6963	Remote Similarity	NPD7549	Discontinued
0.6961	Remote Similarity	NPD4433	Discontinued
0.6959	Remote Similarity	NPD7097	Phase 1
0.6957	Remote Similarity	NPD6234	Discontinued
0.6952	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3823	Discontinued
0.6946	Remote Similarity	NPD4908	Phase 1
0.6944	Remote Similarity	NPD4678	Approved
0.6944	Remote Similarity	NPD4675	Approved
0.694	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD422	Phase 1
0.6932	Remote Similarity	NPD6667	Approved
0.6932	Remote Similarity	NPD6666	Approved
0.6931	Remote Similarity	NPD5844	Phase 1
0.6923	Remote Similarity	NPD7930	Approved
0.6919	Remote Similarity	NPD6746	Phase 2
0.6914	Remote Similarity	NPD7466	Approved
0.6911	Remote Similarity	NPD7240	Approved
0.691	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7411	Suspended
0.69	Remote Similarity	NPD7565	Approved
0.6872	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5403	Approved
0.6866	Remote Similarity	NPD6778	Approved
0.6866	Remote Similarity	NPD6782	Approved
0.6866	Remote Similarity	NPD6780	Approved
0.6866	Remote Similarity	NPD6777	Approved
0.6866	Remote Similarity	NPD6781	Approved
0.6866	Remote Similarity	NPD6779	Approved
0.6866	Remote Similarity	NPD6776	Approved
0.6864	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7999	Approved
0.6857	Remote Similarity	NPD6674	Discontinued
0.6848	Remote Similarity	NPD7773	Phase 2
0.6847	Remote Similarity	NPD7697	Approved
0.6847	Remote Similarity	NPD7696	Phase 3
0.6847	Remote Similarity	NPD7698	Approved
0.6847	Remote Similarity	NPD7435	Discontinued
0.6845	Remote Similarity	NPD7608	Discontinued
0.6831	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7819	Suspended
0.6831	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4666	Phase 3
0.6814	Remote Similarity	NPD7870	Phase 2
0.6814	Remote Similarity	NPD7871	Phase 2
0.6809	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4005	Discontinued
0.6793	Remote Similarity	NPD5402	Approved
0.6793	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5709	Phase 3
0.6768	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5401	Approved
0.676	Remote Similarity	NPD3536	Discontinued
0.676	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6502	Phase 2
0.6757	Remote Similarity	NPD7768	Phase 2
0.6753	Remote Similarity	NPD8312	Approved
0.6753	Remote Similarity	NPD8313	Approved
0.6746	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8150	Discontinued
0.6729	Remote Similarity	NPD8366	Approved
0.6727	Remote Similarity	NPD1610	Phase 2
0.6724	Remote Similarity	NPD7033	Discontinued
0.6724	Remote Similarity	NPD4108	Discontinued
0.6723	Remote Similarity	NPD3750	Approved
0.6722	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6971	Discontinued
0.6715	Remote Similarity	NPD7701	Phase 2
0.6706	Remote Similarity	NPD3027	Phase 3
0.6704	Remote Similarity	NPD4357	Discontinued
0.6703	Remote Similarity	NPD3817	Phase 2
0.6701	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD3490	Discontinued
0.6687	Remote Similarity	NPD1548	Phase 1
0.6686	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4060	Phase 1
0.6686	Remote Similarity	NPD2203	Discontinued
0.6686	Remote Similarity	NPD4993	Discontinued
0.6686	Remote Similarity	NPD6032	Approved
0.6685	Remote Similarity	NPD1934	Approved
0.6685	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6166	Phase 2
0.6684	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6184	Discontinued
0.6684	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4123	Phase 3
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD8059	Phase 3
0.6651	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD8469	Approved
0.665	Remote Similarity	NPD8319	Approved
0.665	Remote Similarity	NPD8320	Phase 1
0.6649	Remote Similarity	NPD5772	Approved
0.6649	Remote Similarity	NPD5773	Approved
0.6649	Remote Similarity	NPD7685	Pre-registration
0.6649	Remote Similarity	NPD5929	Approved
0.6648	Remote Similarity	NPD4003	Phase 3
0.6647	Remote Similarity	NPD6355	Discontinued
0.6647	Remote Similarity	NPD3685	Discontinued
0.6634	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6863	Phase 2
0.6633	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD8031	Discontinued
0.663	Remote Similarity	NPD6677	Suspended
0.663	Remote Similarity	NPD3778	Approved
0.6629	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4628	Phase 3
0.6629	Remote Similarity	NPD5588	Approved
0.6617	Remote Similarity	NPD6535	Approved
0.6617	Remote Similarity	NPD6534	Approved
0.6616	Remote Similarity	NPD1898	Discontinued
0.6615	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6799	Approved
0.6609	Remote Similarity	NPD4097	Suspended
0.6608	Remote Similarity	NPD4625	Phase 3
0.6607	Remote Similarity	NPD3225	Approved
0.6606	Remote Similarity	NPD8491	Approved
0.6602	Remote Similarity	NPD6669	Phase 2
0.6601	Remote Similarity	NPD7699	Phase 2
0.6601	Remote Similarity	NPD7700	Phase 2
0.66	Remote Similarity	NPD3819	Phase 2
0.6598	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2677	Approved
0.6592	Remote Similarity	NPD2219	Phase 1
0.659	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3985	Discontinued
0.6574	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4538	Approved
0.6571	Remote Similarity	NPD4536	Approved
0.6571	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6798	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