NPASS Compound

Structure

CID315913 OpenBabel06191716132D 44 48 0 0 1 0 0 0 0 0999 V2000 -8.9967 6.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4967 5.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 -9.4967 5.4487 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 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 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 13 1 0 0 0 0 3 14 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 2 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 24 1 0 0 0 0 15 27 1 0 0 0 0 16 19 2 0 0 0 0 17 22 1 0 0 0 0 17 24 2 0 0 0 0 18 41 1 0 0 0 0 19 40 1 0 0 0 0 20 40 1 0 0 0 0 21 22 2 0 0 0 0 21 28 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 25 1 0 0 0 0 23 29 1 0 0 0 0 23 35 1 1 0 0 0 24 42 1 0 0 0 0 25 26 1 0 0 0 0 25 43 1 1 0 0 0 26 31 1 0 0 0 0 26 39 1 6 0 0 0 27 33 2 3 0 0 0 27 36 1 0 0 0 0 28 37 2 0 0 0 0 28 42 1 0 0 0 0 29 41 1 6 0 0 0 29 44 1 0 0 0 0 30 32 2 0 0 0 0 30 38 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:	3.852
LogD:	2.647
LogS:	-5.134
# Rotatable Bonds:	9
TPSA:	189.01
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	4.576
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:	-5.697
MDCK Permeability:	1.5832749340916052e-05
Pgp-inhibitor:	0.123
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	90.81822967529297%
Volume Distribution (VD):	1.085
Pgp-substrate:	4.394225597381592%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.287
CYP2C9-inhibitor:	0.174
CYP2C9-substrate:	0.156
CYP2D6-inhibitor:	0.163
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.247
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	2.237
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.96
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.703
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.08
Carcinogencity:	0.229
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.004

Download Data

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

Natural Product: NPC315913

Natural Product ID:	NPC315913
*Common Name:**	Comabiocin B
IUPAC Name:	[(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-8-methyl-2-oxo-3-[(2-propan-2-yl-2,3-dihydro-1-benzofuran-5-carbonyl)amino]chromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] carbamate
Synonyms:
Standard InCHIKey:	YNRLZXZXAKJHIR-KJNXQIJGSA-N
Standard InCHI:	InChI=1S/C31H36N2O11/c1-13(2)20-12-16-11-15(7-9-19(16)40-20)27(36)33-21-22(34)17-8-10-18(14(3)24(17)42-28(21)37)41-29-23(35)25(43-30(32)38)26(39-6)31(4,5)44-29/h7-11,13,20,23,25-26,29,34-35H,12H2,1-6H3,(H2,32,38)(H,33,36)/t20?,23-,25+,26-,29-/m1/s1
SMILES:	CC(C)C1Cc2cc(ccc2O1)C(=Nc1c(c2ccc(c(C)c2oc1=O)O[C@H]1[C@@H]([C@@H]([C@H](C(C)(C)O1)OC)OC(=N)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097288
PubChem CID:	54734318
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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	14.0	mm	PMID[526604]
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	12.0	mm	PMID[526604]
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	10.0	mm	PMID[526604]

☑ 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 NPC315913 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	330
0.1-0.2	1584
0.2-0.3	4555
0.3-0.4	10772
0.4-0.5	7671
0.5-0.6	9396
0.6-0.7	7138
0.7-0.8	1238
0.8-0.85	0
0.85-0.9	6
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC314213
0.9756	High Similarity	NPC314025
0.9697	High Similarity	NPC314656
0.8476	Intermediate Similarity	NPC169510
0.8415	Intermediate Similarity	NPC296377
0.8303	Intermediate Similarity	NPC471764
0.8303	Intermediate Similarity	NPC87950
0.8293	Intermediate Similarity	NPC226722
0.8293	Intermediate Similarity	NPC85624
0.8115	Intermediate Similarity	NPC257266
0.8073	Intermediate Similarity	NPC257728
0.8072	Intermediate Similarity	NPC469701
0.8059	Intermediate Similarity	NPC176186
0.8059	Intermediate Similarity	NPC470264
0.8059	Intermediate Similarity	NPC169404
0.8059	Intermediate Similarity	NPC302610
0.8059	Intermediate Similarity	NPC53587
0.8049	Intermediate Similarity	NPC476442
0.8049	Intermediate Similarity	NPC215512
0.8031	Intermediate Similarity	NPC153365
0.8024	Intermediate Similarity	NPC107120
0.8024	Intermediate Similarity	NPC74320
0.8012	Intermediate Similarity	NPC150442
0.8012	Intermediate Similarity	NPC471824
0.7939	Intermediate Similarity	NPC5155
0.7939	Intermediate Similarity	NPC287286
0.7939	Intermediate Similarity	NPC152771
0.7939	Intermediate Similarity	NPC195357
0.7939	Intermediate Similarity	NPC108674
0.7927	Intermediate Similarity	NPC279573
0.7892	Intermediate Similarity	NPC472353
0.7886	Intermediate Similarity	NPC241600
0.7886	Intermediate Similarity	NPC173726
0.7879	Intermediate Similarity	NPC312881
0.7866	Intermediate Similarity	NPC232246
0.7866	Intermediate Similarity	NPC184861
0.7866	Intermediate Similarity	NPC281014
0.7866	Intermediate Similarity	NPC212124
0.7866	Intermediate Similarity	NPC294456
0.7866	Intermediate Similarity	NPC225106
0.7866	Intermediate Similarity	NPC153818
0.7857	Intermediate Similarity	NPC106126
0.7857	Intermediate Similarity	NPC108994
0.7849	Intermediate Similarity	NPC476352
0.7849	Intermediate Similarity	NPC215060
0.7844	Intermediate Similarity	NPC116922
0.7836	Intermediate Similarity	NPC107197
0.7836	Intermediate Similarity	NPC100818
0.7824	Intermediate Similarity	NPC270751
0.7824	Intermediate Similarity	NPC93924
0.7818	Intermediate Similarity	NPC35501
0.7818	Intermediate Similarity	NPC144512
0.7818	Intermediate Similarity	NPC47040
0.7818	Intermediate Similarity	NPC278600
0.7818	Intermediate Similarity	NPC137262
0.7818	Intermediate Similarity	NPC37428
0.7818	Intermediate Similarity	NPC151946
0.7818	Intermediate Similarity	NPC211110
0.7805	Intermediate Similarity	NPC26954
0.7805	Intermediate Similarity	NPC224543
0.7805	Intermediate Similarity	NPC78746
0.7805	Intermediate Similarity	NPC38099
0.7805	Intermediate Similarity	NPC188380
0.7805	Intermediate Similarity	NPC103409
0.7798	Intermediate Similarity	NPC313414
0.7798	Intermediate Similarity	NPC225445
0.7798	Intermediate Similarity	NPC177597
0.7784	Intermediate Similarity	NPC139976
0.7784	Intermediate Similarity	NPC84207
0.7784	Intermediate Similarity	NPC5253
0.7784	Intermediate Similarity	NPC49542
0.7784	Intermediate Similarity	NPC128337
0.7784	Intermediate Similarity	NPC230718
0.7784	Intermediate Similarity	NPC478269
0.7765	Intermediate Similarity	NPC97240
0.7765	Intermediate Similarity	NPC469700
0.7758	Intermediate Similarity	NPC262328
0.7758	Intermediate Similarity	NPC155963
0.7758	Intermediate Similarity	NPC87777
0.7746	Intermediate Similarity	NPC59692
0.7744	Intermediate Similarity	NPC472525
0.7744	Intermediate Similarity	NPC33986
0.7733	Intermediate Similarity	NPC472710
0.7733	Intermediate Similarity	NPC472709
0.7733	Intermediate Similarity	NPC103116
0.7719	Intermediate Similarity	NPC220282
0.7711	Intermediate Similarity	NPC475836
0.7701	Intermediate Similarity	NPC469699
0.7697	Intermediate Similarity	NPC18189
0.7697	Intermediate Similarity	NPC470936
0.7697	Intermediate Similarity	NPC262585
0.7697	Intermediate Similarity	NPC20829
0.7697	Intermediate Similarity	NPC166180
0.7697	Intermediate Similarity	NPC478267
0.7683	Intermediate Similarity	NPC180716
0.7683	Intermediate Similarity	NPC50896
0.7683	Intermediate Similarity	NPC213173
0.7683	Intermediate Similarity	NPC326600
0.7683	Intermediate Similarity	NPC62366
0.7683	Intermediate Similarity	NPC98179
0.7683	Intermediate Similarity	NPC253574
0.7683	Intermediate Similarity	NPC204353
0.7683	Intermediate Similarity	NPC131950
0.7683	Intermediate Similarity	NPC224475
0.768	Intermediate Similarity	NPC208818
0.7674	Intermediate Similarity	NPC106138
0.767	Intermediate Similarity	NPC228357
0.7661	Intermediate Similarity	NPC52740
0.7661	Intermediate Similarity	NPC175275
0.7651	Intermediate Similarity	NPC124149
0.7647	Intermediate Similarity	NPC43508
0.7647	Intermediate Similarity	NPC475919
0.7647	Intermediate Similarity	NPC474661
0.7647	Intermediate Similarity	NPC476301
0.7644	Intermediate Similarity	NPC197741
0.7644	Intermediate Similarity	NPC18249
0.7644	Intermediate Similarity	NPC10221
0.7644	Intermediate Similarity	NPC140915
0.7644	Intermediate Similarity	NPC187028
0.7644	Intermediate Similarity	NPC476452
0.7644	Intermediate Similarity	NPC305700
0.7636	Intermediate Similarity	NPC471909
0.7636	Intermediate Similarity	NPC281241
0.7636	Intermediate Similarity	NPC472424
0.7636	Intermediate Similarity	NPC471625
0.7636	Intermediate Similarity	NPC86892
0.763	Intermediate Similarity	NPC114740
0.7624	Intermediate Similarity	NPC475621
0.7622	Intermediate Similarity	NPC318400
0.7622	Intermediate Similarity	NPC207002
0.7622	Intermediate Similarity	NPC133956
0.7622	Intermediate Similarity	NPC142563
0.7622	Intermediate Similarity	NPC1220
0.7622	Intermediate Similarity	NPC469965
0.7622	Intermediate Similarity	NPC471910
0.7622	Intermediate Similarity	NPC296624
0.7622	Intermediate Similarity	NPC215037
0.7622	Intermediate Similarity	NPC291551
0.7622	Intermediate Similarity	NPC241165
0.7622	Intermediate Similarity	NPC141822
0.7622	Intermediate Similarity	NPC469449
0.7622	Intermediate Similarity	NPC31849
0.7622	Intermediate Similarity	NPC205797
0.7622	Intermediate Similarity	NPC167111
0.7619	Intermediate Similarity	NPC210192
0.7616	Intermediate Similarity	NPC187398
0.7616	Intermediate Similarity	NPC476348
0.7616	Intermediate Similarity	NPC96294
0.7611	Intermediate Similarity	NPC257566
0.7611	Intermediate Similarity	NPC124155
0.7611	Intermediate Similarity	NPC183672
0.7606	Intermediate Similarity	NPC106700
0.7596	Intermediate Similarity	NPC76047
0.759	Intermediate Similarity	NPC55615
0.759	Intermediate Similarity	NPC471630
0.759	Intermediate Similarity	NPC476455
0.759	Intermediate Similarity	NPC177281
0.759	Intermediate Similarity	NPC149320
0.759	Intermediate Similarity	NPC128529
0.759	Intermediate Similarity	NPC283019
0.759	Intermediate Similarity	NPC160727
0.7588	Intermediate Similarity	NPC471667
0.7588	Intermediate Similarity	NPC79429
0.7588	Intermediate Similarity	NPC217635
0.7586	Intermediate Similarity	NPC213197
0.7586	Intermediate Similarity	NPC259707
0.7584	Intermediate Similarity	NPC470607
0.7584	Intermediate Similarity	NPC43761
0.7576	Intermediate Similarity	NPC319859
0.7576	Intermediate Similarity	NPC287182
0.7576	Intermediate Similarity	NPC127888
0.7576	Intermediate Similarity	NPC164269
0.7576	Intermediate Similarity	NPC307412
0.7576	Intermediate Similarity	NPC117048
0.7576	Intermediate Similarity	NPC267412
0.7576	Intermediate Similarity	NPC124085
0.7576	Intermediate Similarity	NPC223008
0.7576	Intermediate Similarity	NPC166672
0.7576	Intermediate Similarity	NPC115335
0.7576	Intermediate Similarity	NPC84894
0.7576	Intermediate Similarity	NPC47163
0.7576	Intermediate Similarity	NPC225696
0.7576	Intermediate Similarity	NPC74655
0.7576	Intermediate Similarity	NPC18804
0.7576	Intermediate Similarity	NPC100986
0.7576	Intermediate Similarity	NPC198154
0.7576	Intermediate Similarity	NPC195343
0.7576	Intermediate Similarity	NPC55149
0.7576	Intermediate Similarity	NPC260265
0.7576	Intermediate Similarity	NPC198381
0.7576	Intermediate Similarity	NPC296915
0.7576	Intermediate Similarity	NPC97834
0.7574	Intermediate Similarity	NPC178466
0.7574	Intermediate Similarity	NPC63628
0.7574	Intermediate Similarity	NPC145319
0.7571	Intermediate Similarity	NPC284810
0.7571	Intermediate Similarity	NPC473323
0.7571	Intermediate Similarity	NPC17521
0.7569	Intermediate Similarity	NPC72016
0.7561	Intermediate Similarity	NPC14248

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 NPC315913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	636
0.2-0.3	1126
0.3-0.4	2199
0.4-0.5	2862
0.5-0.6	1675
0.6-0.7	377
0.7-0.8	43
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
0.8115	Intermediate Similarity	NPD7583	Approved
0.8073	Intermediate Similarity	NPD7585	Approved
0.7849	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD7584	Approved
0.7622	Intermediate Similarity	NPD5124	Phase 1
0.7622	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1653	Approved
0.7446	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6559	Discontinued
0.7313	Intermediate Similarity	NPD8151	Discontinued
0.7273	Intermediate Similarity	NPD6823	Phase 2
0.7263	Intermediate Similarity	NPD8455	Phase 2
0.7209	Intermediate Similarity	NPD1652	Phase 2
0.7208	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7228	Approved
0.7166	Intermediate Similarity	NPD7054	Approved
0.7157	Intermediate Similarity	NPD7783	Phase 2
0.7157	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7801	Approved
0.7151	Intermediate Similarity	NPD6072	Discontinued
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7128	Intermediate Similarity	NPD7472	Approved
0.7128	Intermediate Similarity	NPD7074	Phase 3
0.7126	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD3818	Discontinued
0.7111	Intermediate Similarity	NPD37	Approved
0.7095	Intermediate Similarity	NPD4380	Phase 2
0.7093	Intermediate Similarity	NPD7266	Discontinued
0.7088	Intermediate Similarity	NPD4967	Phase 2
0.7088	Intermediate Similarity	NPD4965	Approved
0.7088	Intermediate Similarity	NPD4966	Approved
0.7072	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7251	Discontinued
0.7052	Intermediate Similarity	NPD2424	Discontinued
0.7039	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD2415	Discontinued
0.7027	Intermediate Similarity	NPD7199	Phase 2
0.7024	Intermediate Similarity	NPD1048	Approved
0.7018	Intermediate Similarity	NPD7097	Phase 1
0.7017	Intermediate Similarity	NPD6801	Discontinued
0.7016	Intermediate Similarity	NPD7808	Phase 3
0.7016	Intermediate Similarity	NPD7549	Discontinued
0.7016	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6234	Discontinued
0.701	Intermediate Similarity	NPD6842	Approved
0.701	Intermediate Similarity	NPD6841	Approved
0.701	Intermediate Similarity	NPD6843	Phase 3
0.7006	Intermediate Similarity	NPD7447	Phase 1
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD7007	Discovery
0.7	Intermediate Similarity	NPD6797	Phase 2
0.6994	Remote Similarity	NPD1091	Approved
0.6989	Remote Similarity	NPD6666	Approved
0.6989	Remote Similarity	NPD5058	Phase 3
0.6989	Remote Similarity	NPD6667	Approved
0.6971	Remote Similarity	NPD7930	Approved
0.6971	Remote Similarity	NPD7466	Approved
0.6966	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7240	Approved
0.6949	Remote Similarity	NPD7213	Phase 3
0.6949	Remote Similarity	NPD7212	Phase 2
0.6942	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7874	Approved
0.6941	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1613	Approved
0.6923	Remote Similarity	NPD4433	Discontinued
0.6915	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6674	Discontinued
0.6911	Remote Similarity	NPD3823	Discontinued
0.6906	Remote Similarity	NPD4678	Approved
0.6906	Remote Similarity	NPD4675	Approved
0.6902	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7608	Discontinued
0.6895	Remote Similarity	NPD5844	Phase 1
0.689	Remote Similarity	NPD422	Phase 1
0.6885	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6746	Phase 2
0.6868	Remote Similarity	NPD7411	Suspended
0.6866	Remote Similarity	NPD7565	Approved
0.6862	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5403	Approved
0.6832	Remote Similarity	NPD6781	Approved
0.6832	Remote Similarity	NPD6778	Approved
0.6832	Remote Similarity	NPD6782	Approved
0.6832	Remote Similarity	NPD6777	Approved
0.6832	Remote Similarity	NPD6776	Approved
0.6832	Remote Similarity	NPD6780	Approved
0.6832	Remote Similarity	NPD6779	Approved
0.6829	Remote Similarity	NPD7999	Approved
0.6824	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7435	Discontinued
0.6814	Remote Similarity	NPD7696	Phase 3
0.6814	Remote Similarity	NPD7697	Approved
0.6814	Remote Similarity	NPD7698	Approved
0.6813	Remote Similarity	NPD6502	Phase 2
0.6811	Remote Similarity	NPD7773	Phase 2
0.6804	Remote Similarity	NPD8312	Approved
0.6804	Remote Similarity	NPD8313	Approved
0.6793	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7819	Suspended
0.6791	Remote Similarity	NPD4666	Phase 3
0.6788	Remote Similarity	NPD1610	Phase 2
0.6786	Remote Similarity	NPD8150	Discontinued
0.6782	Remote Similarity	NPD4108	Discontinued
0.678	Remote Similarity	NPD7871	Phase 2
0.678	Remote Similarity	NPD7870	Phase 2
0.6776	Remote Similarity	NPD8366	Approved
0.6763	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4005	Discontinued
0.6757	Remote Similarity	NPD5402	Approved
0.6753	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2203	Discontinued
0.6744	Remote Similarity	NPD4060	Phase 1
0.6738	Remote Similarity	NPD5709	Phase 3
0.6735	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5401	Approved
0.6722	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD3536	Discontinued
0.672	Remote Similarity	NPD7768	Phase 2
0.6707	Remote Similarity	NPD3685	Discontinued
0.6706	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6355	Discontinued
0.6703	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7685	Pre-registration
0.6699	Remote Similarity	NPD8320	Phase 1
0.6699	Remote Similarity	NPD8319	Approved
0.6697	Remote Similarity	NPD8469	Approved
0.6686	Remote Similarity	NPD7033	Discontinued
0.6685	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3750	Approved
0.6685	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6677	Suspended
0.6684	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6971	Discontinued
0.6683	Remote Similarity	NPD7701	Phase 2
0.6683	Remote Similarity	NPD6863	Phase 2
0.6667	Remote Similarity	NPD4097	Suspended
0.6667	Remote Similarity	NPD3490	Discontinued
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4357	Discontinued
0.6651	Remote Similarity	NPD8491	Approved
0.6649	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6184	Discontinued
0.6649	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6166	Phase 2
0.6649	Remote Similarity	NPD1934	Approved
0.6648	Remote Similarity	NPD6032	Approved
0.6647	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4993	Discontinued
0.6646	Remote Similarity	NPD1548	Phase 1
0.6633	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4123	Phase 3
0.6628	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2797	Approved
0.6621	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD8059	Phase 3
0.6614	Remote Similarity	NPD5494	Approved
0.6613	Remote Similarity	NPD5772	Approved
0.6613	Remote Similarity	NPD5929	Approved
0.6613	Remote Similarity	NPD5773	Approved
0.6612	Remote Similarity	NPD4003	Phase 3
0.661	Remote Similarity	NPD5762	Approved
0.661	Remote Similarity	NPD5763	Approved
0.6606	Remote Similarity	NPD8067	Phase 3
0.6601	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5557	Phase 1
0.6596	Remote Similarity	NPD8070	Approved
0.6596	Remote Similarity	NPD8031	Discontinued
0.6595	Remote Similarity	NPD3778	Approved
0.6593	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD52	Approved
0.6593	Remote Similarity	NPD7526	Approved
0.6592	Remote Similarity	NPD4628	Phase 3
0.6592	Remote Similarity	NPD6331	Phase 2
0.6591	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5588	Approved
0.6584	Remote Similarity	NPD6534	Approved
0.6584	Remote Similarity	NPD6535	Approved
0.6583	Remote Similarity	NPD1898	Discontinued
0.658	Remote Similarity	NPD3909	Discontinued
0.6579	Remote Similarity	NPD8127	Discontinued
0.6576	Remote Similarity	NPD7458	Discontinued
0.6575	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6799	Approved
0.657	Remote Similarity	NPD4625	Phase 3
0.657	Remote Similarity	NPD6669	Phase 2
0.6569	Remote Similarity	NPD7700	Phase 2
0.6569	Remote Similarity	NPD7699	Phase 2
0.6568	Remote Similarity	NPD3225	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