NPASS Compound

Structure

NPC469315 OpenBabel07101718272D 40 44 0 0 1 0 0 0 0 0999 V2000 -3.6770 0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3809 -2.8328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5165 1.4660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0278 0.6196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8805 1.8676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1542 1.2136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4016 2.2703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1256 -0.5908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2319 2.4433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0215 -1.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6928 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0496 -1.4446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8464 -0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0290 -1.1770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6928 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6787 2.2004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3750 -0.4508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3369 -2.6296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4190 -0.6540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6928 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8464 1.4660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9849 -0.9738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6928 0.9773 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 2.5273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9773 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.2869 -0.0444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5391 2.4433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 1.4660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0837 0.9116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8464 1.4660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8464 -0.4887 0.0000 C 0 0 2 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 -5.9908 -3.3559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.5046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6928 2.9319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3855 2.9319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6389 -1.7001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6787 2.2004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0132 0.6096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 8 32 1 0 0 0 0 10 37 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 32 1 0 0 0 0 14 33 1 0 0 0 0 15 18 1 0 0 0 0 16 21 1 0 0 0 0 17 25 1 0 0 0 0 17 31 1 0 0 0 0 18 1 1 1 0 0 0 18 20 1 0 0 0 0 19 34 2 0 0 0 0 19 38 1 0 0 0 0 20 21 2 0 0 0 0 21 32 1 0 0 0 0 22 16 1 6 0 0 0 22 26 1 0 0 0 0 22 39 1 0 0 0 0 23 15 1 6 0 0 0 23 38 1 0 0 0 0 24 29 1 0 0 0 0 24 31 1 0 0 0 0 25 35 2 0 0 0 0 25 39 1 0 0 0 0 26 31 1 0 0 0 0 26 33 1 0 0 0 0 27 23 1 1 0 0 0 27 30 1 0 0 0 0 27 40 1 0 0 0 0 28 29 1 0 0 0 0 28 36 2 0 0 0 0 28 37 1 0 0 0 0 30 40 1 0 0 0 0 31 7 1 6 0 0 0 32 33 1 1 0 0 0 33 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.36
Volume:	564.078
LogP:	4.643
LogD:	3.619
LogS:	-4.78
# Rotatable Bonds:	6
TPSA:	96.36
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.281
Synthetic Accessibility Score:	5.418
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
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:	-5.203
MDCK Permeability:	1.690992939984426e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.223
Plasma Protein Binding (PPB):	92.26526641845703%
Volume Distribution (VD):	1.517
Pgp-substrate:	3.810407876968384%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.232
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.642
CYP3A4-substrate:	0.765

ADMET: Excretion

Clearance (CL):	5.366
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.361
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.517
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.049
Carcinogencity:	0.116
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC469315

Natural Product ID:	NPC469315
*Common Name:**	OZHUDGIWAKILEA-SUCCYQEWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OZHUDGIWAKILEA-SUCCYQEWSA-N
Standard InCHI:	InChI=1S/C33H50O7/c1-18(15-23(38-19(2)34)27-30(5,6)40-27)20-11-13-32(8)21(20)16-22-26-31(7,17-25(35)39-22)24(12-14-33(26,32)9)29(3,4)28(36)37-10/h18,22-24,26-27H,11-17H2,1-10H3/t18-,22+,23+,24?,26?,27-,31+,32+,33+/m1/s1
SMILES:	COC(=O)C(C1CC[C@]2(C3[C@@]1(C)CC(=O)O[C@H]3CC1=C(CC[C@]21C)[C@@H](C[C@@H]([C@H]1OC1(C)C)OC(=O)C)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL102639
PubChem CID:	44335337
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
IC50	1
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	-2.6	%	PMID[492174]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	17.2	%	PMID[492174]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	49.2	%	PMID[492174]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	84.2	%	PMID[492174]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	110.3	%	PMID[492174]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	10000.0	nM	PMID[492174]

☑ 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 NPC469315 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	265
0.1-0.2	1815
0.2-0.3	6014
0.3-0.4	14848
0.4-0.5	7512
0.5-0.6	6117
0.6-0.7	5206
0.7-0.8	882
0.8-0.85	20
0.85-0.9	12
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9663	High Similarity	NPC471822
0.9043	High Similarity	NPC469327
0.9022	High Similarity	NPC471777
0.9011	High Similarity	NPC240617
0.871	High Similarity	NPC473415
0.871	High Similarity	NPC469329
0.871	High Similarity	NPC37787
0.871	High Similarity	NPC180557
0.871	High Similarity	NPC30677
0.8586	High Similarity	NPC9457
0.8586	High Similarity	NPC471783
0.8557	High Similarity	NPC469316
0.8495	Intermediate Similarity	NPC274046
0.8495	Intermediate Similarity	NPC198074
0.8485	Intermediate Similarity	NPC470587
0.8438	Intermediate Similarity	NPC471582
0.8387	Intermediate Similarity	NPC473166
0.8298	Intermediate Similarity	NPC79117
0.8283	Intermediate Similarity	NPC324001
0.8235	Intermediate Similarity	NPC41405
0.7981	Intermediate Similarity	NPC5284
0.7979	Intermediate Similarity	NPC469323
0.7959	Intermediate Similarity	NPC292133
0.7957	Intermediate Similarity	NPC469314
0.7957	Intermediate Similarity	NPC469317
0.7957	Intermediate Similarity	NPC241875
0.7957	Intermediate Similarity	NPC469322
0.7944	Intermediate Similarity	NPC243981
0.7925	Intermediate Similarity	NPC255017
0.7921	Intermediate Similarity	NPC264048
0.7917	Intermediate Similarity	NPC474185
0.7895	Intermediate Similarity	NPC471896
0.7895	Intermediate Similarity	NPC20388
0.7885	Intermediate Similarity	NPC218853
0.7879	Intermediate Similarity	NPC471784
0.7879	Intermediate Similarity	NPC303777
0.7872	Intermediate Similarity	NPC80335
0.7864	Intermediate Similarity	NPC469318
0.7864	Intermediate Similarity	NPC180744
0.7864	Intermediate Similarity	NPC473173
0.7864	Intermediate Similarity	NPC473165
0.7857	Intermediate Similarity	NPC327788
0.7857	Intermediate Similarity	NPC471775
0.7849	Intermediate Similarity	NPC264127
0.7843	Intermediate Similarity	NPC471293
0.7835	Intermediate Similarity	NPC159410
0.783	Intermediate Similarity	NPC234042
0.783	Intermediate Similarity	NPC152117
0.7826	Intermediate Similarity	NPC109512
0.7822	Intermediate Similarity	NPC473163
0.7812	Intermediate Similarity	NPC474631
0.7812	Intermediate Similarity	NPC49420
0.7812	Intermediate Similarity	NPC26888
0.781	Intermediate Similarity	NPC250956
0.7789	Intermediate Similarity	NPC474679
0.7789	Intermediate Similarity	NPC474889
0.7778	Intermediate Similarity	NPC23680
0.7767	Intermediate Similarity	NPC472655
0.7766	Intermediate Similarity	NPC162107
0.7766	Intermediate Similarity	NPC46912
0.7755	Intermediate Similarity	NPC279974
0.7755	Intermediate Similarity	NPC473170
0.7742	Intermediate Similarity	NPC98270
0.7736	Intermediate Similarity	NPC470960
0.7732	Intermediate Similarity	NPC477435
0.7732	Intermediate Similarity	NPC477436
0.7727	Intermediate Similarity	NPC161065
0.7723	Intermediate Similarity	NPC476897
0.7714	Intermediate Similarity	NPC474242
0.7708	Intermediate Similarity	NPC111585
0.7708	Intermediate Similarity	NPC161638
0.7708	Intermediate Similarity	NPC175628
0.7708	Intermediate Similarity	NPC148414
0.77	Intermediate Similarity	NPC475876
0.77	Intermediate Similarity	NPC470068
0.77	Intermediate Similarity	NPC119036
0.7685	Intermediate Similarity	NPC284915
0.7684	Intermediate Similarity	NPC97884
0.7684	Intermediate Similarity	NPC472220
0.7677	Intermediate Similarity	NPC471039
0.7677	Intermediate Similarity	NPC120708
0.767	Intermediate Similarity	NPC65523
0.766	Intermediate Similarity	NPC73038
0.766	Intermediate Similarity	NPC9892
0.766	Intermediate Similarity	NPC325594
0.766	Intermediate Similarity	NPC91525
0.766	Intermediate Similarity	NPC10005
0.766	Intermediate Similarity	NPC329943
0.7658	Intermediate Similarity	NPC241192
0.7653	Intermediate Similarity	NPC471040
0.7653	Intermediate Similarity	NPC477439
0.7653	Intermediate Similarity	NPC473435
0.7653	Intermediate Similarity	NPC473431
0.7653	Intermediate Similarity	NPC476716
0.7653	Intermediate Similarity	NPC296164
0.7653	Intermediate Similarity	NPC473280
0.7653	Intermediate Similarity	NPC471078
0.7647	Intermediate Similarity	NPC296879
0.7647	Intermediate Similarity	NPC471119
0.7647	Intermediate Similarity	NPC475558
0.7647	Intermediate Similarity	NPC473928
0.7647	Intermediate Similarity	NPC473788
0.7642	Intermediate Similarity	NPC472215
0.7642	Intermediate Similarity	NPC472214
0.7642	Intermediate Similarity	NPC253906
0.7634	Intermediate Similarity	NPC475509
0.7629	Intermediate Similarity	NPC285184
0.7629	Intermediate Similarity	NPC470590
0.7629	Intermediate Similarity	NPC60755
0.7629	Intermediate Similarity	NPC77099
0.7615	Intermediate Similarity	NPC298278
0.7615	Intermediate Similarity	NPC270929
0.7604	Intermediate Similarity	NPC475921
0.7604	Intermediate Similarity	NPC469866
0.7604	Intermediate Similarity	NPC474704
0.7604	Intermediate Similarity	NPC475049
0.7604	Intermediate Similarity	NPC30522
0.7604	Intermediate Similarity	NPC471342
0.76	Intermediate Similarity	NPC110937
0.76	Intermediate Similarity	NPC469810
0.76	Intermediate Similarity	NPC84335
0.76	Intermediate Similarity	NPC158347
0.76	Intermediate Similarity	NPC38530
0.7596	Intermediate Similarity	NPC475414
0.7596	Intermediate Similarity	NPC173172
0.7589	Intermediate Similarity	NPC204731
0.7576	Intermediate Similarity	NPC477437
0.7576	Intermediate Similarity	NPC470016
0.7576	Intermediate Similarity	NPC195715
0.7576	Intermediate Similarity	NPC84383
0.7576	Intermediate Similarity	NPC473648
0.7576	Intermediate Similarity	NPC317586
0.7576	Intermediate Similarity	NPC477438
0.7573	Intermediate Similarity	NPC55954
0.7573	Intermediate Similarity	NPC218513
0.757	Intermediate Similarity	NPC469656
0.757	Intermediate Similarity	NPC474846
0.757	Intermediate Similarity	NPC469655
0.7551	Intermediate Similarity	NPC107674
0.7551	Intermediate Similarity	NPC86368
0.7551	Intermediate Similarity	NPC170220
0.7551	Intermediate Similarity	NPC141497
0.7549	Intermediate Similarity	NPC233012
0.7549	Intermediate Similarity	NPC54909
0.7549	Intermediate Similarity	NPC470054
0.7547	Intermediate Similarity	NPC173905
0.7547	Intermediate Similarity	NPC477070
0.7547	Intermediate Similarity	NPC284828
0.7547	Intermediate Similarity	NPC477069
0.7547	Intermediate Similarity	NPC5475
0.7547	Intermediate Similarity	NPC469370
0.7547	Intermediate Similarity	NPC472216
0.7527	Intermediate Similarity	NPC475622
0.7527	Intermediate Similarity	NPC108045
0.7527	Intermediate Similarity	NPC139206
0.7527	Intermediate Similarity	NPC86370
0.7526	Intermediate Similarity	NPC473269
0.7526	Intermediate Similarity	NPC475965
0.7526	Intermediate Similarity	NPC120840
0.7526	Intermediate Similarity	NPC474728
0.7526	Intermediate Similarity	NPC474842
0.7526	Intermediate Similarity	NPC113989
0.7526	Intermediate Similarity	NPC328141
0.7525	Intermediate Similarity	NPC470067
0.7525	Intermediate Similarity	NPC472028
0.7525	Intermediate Similarity	NPC275439
0.7525	Intermediate Similarity	NPC112753
0.7525	Intermediate Similarity	NPC58942
0.7525	Intermediate Similarity	NPC470066
0.7525	Intermediate Similarity	NPC477854
0.7525	Intermediate Similarity	NPC260149
0.7524	Intermediate Similarity	NPC475176
0.7524	Intermediate Similarity	NPC59530
0.7523	Intermediate Similarity	NPC472274
0.75	Intermediate Similarity	NPC224145
0.75	Intermediate Similarity	NPC327179
0.75	Intermediate Similarity	NPC476163
0.75	Intermediate Similarity	NPC255176
0.75	Intermediate Similarity	NPC189616
0.75	Intermediate Similarity	NPC4309
0.75	Intermediate Similarity	NPC149124
0.75	Intermediate Similarity	NPC242864
0.75	Intermediate Similarity	NPC222834
0.75	Intermediate Similarity	NPC280782
0.75	Intermediate Similarity	NPC230151
0.75	Intermediate Similarity	NPC470063
0.75	Intermediate Similarity	NPC75531
0.75	Intermediate Similarity	NPC473175
0.75	Intermediate Similarity	NPC307164
0.7477	Intermediate Similarity	NPC473720
0.7477	Intermediate Similarity	NPC329736
0.7477	Intermediate Similarity	NPC239097
0.7477	Intermediate Similarity	NPC470065
0.7476	Intermediate Similarity	NPC470053
0.7475	Intermediate Similarity	NPC174051
0.7475	Intermediate Similarity	NPC23621
0.7475	Intermediate Similarity	NPC166906
0.7475	Intermediate Similarity	NPC184006
0.7475	Intermediate Similarity	NPC67831
0.7475	Intermediate Similarity	NPC269729

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 NPC469315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	2207
0.2-0.3	3932
0.3-0.4	1880
0.4-0.5	492
0.5-0.6	233
0.6-0.7	163
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7596	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.7429	Intermediate Similarity	NPD5739	Approved
0.7429	Intermediate Similarity	NPD6675	Approved
0.7429	Intermediate Similarity	NPD7128	Approved
0.7429	Intermediate Similarity	NPD6402	Approved
0.7396	Intermediate Similarity	NPD3573	Approved
0.7374	Intermediate Similarity	NPD6399	Phase 3
0.7358	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7900	Approved
0.73	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7748	Approved
0.7292	Intermediate Similarity	NPD7521	Approved
0.7292	Intermediate Similarity	NPD7146	Approved
0.7292	Intermediate Similarity	NPD6409	Approved
0.7292	Intermediate Similarity	NPD6684	Approved
0.7292	Intermediate Similarity	NPD5330	Approved
0.7292	Intermediate Similarity	NPD7334	Approved
0.729	Intermediate Similarity	NPD7320	Approved
0.729	Intermediate Similarity	NPD6899	Approved
0.729	Intermediate Similarity	NPD6881	Approved
0.7273	Intermediate Similarity	NPD8035	Phase 2
0.7273	Intermediate Similarity	NPD8034	Phase 2
0.7248	Intermediate Similarity	NPD8130	Phase 1
0.7232	Intermediate Similarity	NPD7115	Discovery
0.7228	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6372	Approved
0.7222	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6373	Approved
0.7196	Intermediate Similarity	NPD5697	Approved
0.7196	Intermediate Similarity	NPD5701	Approved
0.7156	Intermediate Similarity	NPD7102	Approved
0.7156	Intermediate Similarity	NPD6883	Approved
0.7156	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6411	Approved
0.7091	Intermediate Similarity	NPD6869	Approved
0.7091	Intermediate Similarity	NPD6650	Approved
0.7091	Intermediate Similarity	NPD6649	Approved
0.7091	Intermediate Similarity	NPD6847	Approved
0.7091	Intermediate Similarity	NPD6617	Approved
0.7087	Intermediate Similarity	NPD7902	Approved
0.708	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5328	Approved
0.7064	Intermediate Similarity	NPD6012	Approved
0.7064	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6014	Approved
0.7064	Intermediate Similarity	NPD6013	Approved
0.7027	Intermediate Similarity	NPD6882	Approved
0.701	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6011	Approved
0.6939	Remote Similarity	NPD6098	Approved
0.6937	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6079	Approved
0.6931	Remote Similarity	NPD7515	Phase 2
0.6923	Remote Similarity	NPD6084	Phase 2
0.6923	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD4755	Approved
0.6907	Remote Similarity	NPD4786	Approved
0.6907	Remote Similarity	NPD3668	Phase 3
0.69	Remote Similarity	NPD6101	Approved
0.69	Remote Similarity	NPD6080	Approved
0.69	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6673	Approved
0.69	Remote Similarity	NPD6904	Approved
0.6875	Remote Similarity	NPD3667	Approved
0.6857	Remote Similarity	NPD7638	Approved
0.6818	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4632	Approved
0.6796	Remote Similarity	NPD6001	Approved
0.6792	Remote Similarity	NPD7639	Approved
0.6792	Remote Similarity	NPD5285	Approved
0.6792	Remote Similarity	NPD4696	Approved
0.6792	Remote Similarity	NPD4700	Approved
0.6792	Remote Similarity	NPD5286	Approved
0.6792	Remote Similarity	NPD7640	Approved
0.6774	Remote Similarity	NPD6117	Approved
0.6768	Remote Similarity	NPD3618	Phase 1
0.6752	Remote Similarity	NPD6319	Approved
0.675	Remote Similarity	NPD7507	Approved
0.6731	Remote Similarity	NPD5695	Phase 3
0.6723	Remote Similarity	NPD7604	Phase 2
0.6703	Remote Similarity	NPD5777	Approved
0.6702	Remote Similarity	NPD6116	Phase 1
0.6701	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4225	Approved
0.6698	Remote Similarity	NPD5696	Approved
0.6696	Remote Similarity	NPD6274	Approved
0.6694	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD3702	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6638	Remote Similarity	NPD6009	Approved
0.6634	Remote Similarity	NPD5208	Approved
0.6632	Remote Similarity	NPD6697	Approved
0.6632	Remote Similarity	NPD6115	Approved
0.6632	Remote Similarity	NPD6118	Approved
0.6632	Remote Similarity	NPD6114	Approved
0.6612	Remote Similarity	NPD6616	Approved
0.661	Remote Similarity	NPD6054	Approved
0.661	Remote Similarity	NPD6059	Approved
0.6606	Remote Similarity	NPD5174	Approved
0.6606	Remote Similarity	NPD5175	Approved
0.6604	Remote Similarity	NPD5173	Approved
0.6602	Remote Similarity	NPD6050	Approved
0.6602	Remote Similarity	NPD5693	Phase 1
0.6585	Remote Similarity	NPD7319	Approved
0.6583	Remote Similarity	NPD8328	Phase 3
0.6581	Remote Similarity	NPD6335	Approved
0.6577	Remote Similarity	NPD6412	Phase 2
0.6574	Remote Similarity	NPD5223	Approved
0.6569	Remote Similarity	NPD6051	Approved
0.6559	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7078	Approved
0.6555	Remote Similarity	NPD5983	Phase 2
0.6555	Remote Similarity	NPD6909	Approved
0.6555	Remote Similarity	NPD6908	Approved
0.6552	Remote Similarity	NPD6868	Approved
0.6545	Remote Similarity	NPD5141	Approved
0.6538	Remote Similarity	NPD4202	Approved
0.6522	Remote Similarity	NPD8133	Approved
0.6518	Remote Similarity	NPD6686	Approved
0.6505	Remote Similarity	NPD5692	Phase 3
0.65	Remote Similarity	NPD1694	Approved
0.65	Remote Similarity	NPD6370	Approved
0.6496	Remote Similarity	NPD6317	Approved
0.6495	Remote Similarity	NPD7525	Registered
0.6486	Remote Similarity	NPD4767	Approved
0.6486	Remote Similarity	NPD4768	Approved
0.6475	Remote Similarity	NPD6336	Discontinued
0.6455	Remote Similarity	NPD4754	Approved
0.6442	Remote Similarity	NPD5694	Approved
0.6441	Remote Similarity	NPD6314	Approved
0.6441	Remote Similarity	NPD6313	Approved
0.6436	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6016	Approved
0.6417	Remote Similarity	NPD6015	Approved
0.6408	Remote Similarity	NPD4753	Phase 2
0.6404	Remote Similarity	NPD4634	Approved
0.64	Remote Similarity	NPD3133	Approved
0.64	Remote Similarity	NPD3666	Approved
0.64	Remote Similarity	NPD3665	Phase 1
0.6381	Remote Similarity	NPD5779	Approved
0.6381	Remote Similarity	NPD5778	Approved
0.6372	Remote Similarity	NPD5128	Approved
0.6372	Remote Similarity	NPD4730	Approved
0.6372	Remote Similarity	NPD4729	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6355	Remote Similarity	NPD7732	Phase 3
0.6346	Remote Similarity	NPD5207	Approved
0.6337	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3703	Phase 2
0.6296	Remote Similarity	NPD5959	Approved
0.6289	Remote Similarity	NPD3617	Approved
0.6281	Remote Similarity	NPD8033	Approved
0.6281	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6422	Discontinued
0.6273	Remote Similarity	NPD4159	Approved
0.6262	Remote Similarity	NPD5654	Approved
0.6261	Remote Similarity	NPD5249	Phase 3
0.6261	Remote Similarity	NPD5248	Approved
0.6261	Remote Similarity	NPD5247	Approved
0.6261	Remote Similarity	NPD5251	Approved
0.6261	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7645	Phase 2
0.6207	Remote Similarity	NPD5215	Approved
0.6207	Remote Similarity	NPD5217	Approved
0.6207	Remote Similarity	NPD5216	Approved
0.6204	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4221	Approved
0.62	Remote Similarity	NPD6435	Approved
0.62	Remote Similarity	NPD4223	Phase 3
0.6198	Remote Similarity	NPD8294	Approved
0.6198	Remote Similarity	NPD8377	Approved
0.619	Remote Similarity	NPD6698	Approved
0.619	Remote Similarity	NPD46	Approved
0.6176	Remote Similarity	NPD5329	Approved
0.617	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7328	Approved
0.6167	Remote Similarity	NPD7327	Approved
0.6161	Remote Similarity	NPD6052	Approved
0.6154	Remote Similarity	NPD6053	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