NPASS Compound

Structure

CID252960 OpenBabel06191716052D 24 28 0 0 1 0 0 0 0 0999 V2000 -1.7498 -2.7185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7293 -4.7590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6976 -3.0342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7025 -2.0260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0147 -3.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5882 0.4918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5784 -1.5255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -1.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0090 -0.5286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8277 -3.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7123 -0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7074 -1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4593 -0.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4544 -1.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0098 -2.0177 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0049 -1.0086 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8470 0.4913 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8373 -1.5085 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0371 -2.0127 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 1.4913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8176 -4.4522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4201 0.2903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4122 -1.3418 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 19 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 5 10 1 0 0 0 0 5 15 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 8 19 1 0 0 0 0 9 22 1 0 0 0 0 9 23 1 0 0 0 0 10 21 1 1 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 18 1 6 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 18 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	331.14
Volume:	321.504
LogP:	1.042
LogD:	1.312
LogS:	-2.151
# Rotatable Bonds:	1
TPSA:	60.39
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.784
Synthetic Accessibility Score:	5.233
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.898
MDCK Permeability:	2.197606590925716e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.385
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.127

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	33.57063293457031%
Volume Distribution (VD):	1.679
Pgp-substrate:	70.89485168457031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.685
CYP2D6-substrate:	0.847
CYP3A4-inhibitor:	0.848
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	7.265
Half-life (T1/2):	0.575

ADMET: Toxicity

hERG Blockers:	0.171
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.443
Rat Oral Acute Toxicity:	0.483
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.59
Carcinogencity:	0.813
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC252960

Natural Product ID:	NPC252960
*Common Name:**	Pretazettine
IUPAC Name:	n.a.
Synonyms:	Pretazettine
Standard InCHIKey:	KLJOYDMUWKSYBP-WXNLUCNWSA-N
Standard InCHI:	InChI=1S/C18H21NO5/c1-19-8-16-18(4-3-10(21-2)5-15(18)19)12-7-14-13(22-9-23-14)6-11(12)17(20)24-16/h3-4,6-7,10,15-17,20H,5,8-9H2,1-2H3/t10-,15+,16+,17?,18+/m1/s1
SMILES:	CN1C[C@H]2[C@@]3(C=C[C@H](C[C@H]13)OC)c1cc3c(cc1C(O)O2)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL606758
PubChem CID:	10314625
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004124] Tazettine-type amaryllidaceae alkaloids

*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
NPO33168	amaryllidaceae isoquinoline	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1336040]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	Turkey	n.a.	PMID[19299148]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510636]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	whole plants	n.a.	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2348199]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26913788]
NPO9942.1	Narcissus tazetta var. chinensis	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4166	Pancratium biflorum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7850.1	Schisandra propinqua var. intermedia	Varieties	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9942.1	Narcissus tazetta var. chinensis	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4166	Pancratium biflorum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4166	Pancratium biflorum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Others	5

Activity Type	# Activity
Organism	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	IC50	=	0.6	ug.mL-1	PMID[455084]
NPT4327	Organism	Yellow fever virus	Yellow fever virus	IC50	=	0.5	ug.mL-1	PMID[455084]
NPT27	Others	Unspecified		TI	=	3.8	n.a.	PMID[455084]
NPT27	Others	Unspecified		TI	=	5.6	n.a.	PMID[455084]
NPT341	Organism	Punta Toro virus	Punta Toro virus	IC50	=	0.61	ug.mL-1	PMID[455084]
NPT4329	Organism	Rift Valley fever virus	Rift Valley fever virus	IC50	=	2.9	ug.mL-1	PMID[455084]
NPT4330	Organism	Sandfly fever sicilian virus	Sandfly fever sicilian virus	IC50	=	0.82	ug.mL-1	PMID[455084]
NPT27	Others	Unspecified		TI	=	3.7	n.a.	PMID[455084]
NPT27	Others	Unspecified		TI	=	3.5	n.a.	PMID[455084]
NPT27	Others	Unspecified		TI	=	3.0	n.a.	PMID[455084]

☑ 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 NPC252960 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	258
0.1-0.2	1229
0.2-0.3	3791
0.3-0.4	11311
0.4-0.5	8201
0.5-0.6	12473
0.6-0.7	4400
0.7-0.8	908
0.8-0.85	61
0.85-0.9	48
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC218614
0.9437	High Similarity	NPC477640
0.9437	High Similarity	NPC225597
0.9437	High Similarity	NPC470739
0.9375	High Similarity	NPC474475
0.9313	High Similarity	NPC58766
0.9313	High Similarity	NPC475686
0.9313	High Similarity	NPC82533
0.9313	High Similarity	NPC290759
0.9313	High Similarity	NPC266176
0.9313	High Similarity	NPC158148
0.9177	High Similarity	NPC4304
0.9146	High Similarity	NPC474470
0.8938	High Similarity	NPC97072
0.8938	High Similarity	NPC215829
0.8922	High Similarity	NPC244554
0.8896	High Similarity	NPC100566
0.8889	High Similarity	NPC247972
0.881	High Similarity	NPC99179
0.878	High Similarity	NPC181653
0.878	High Similarity	NPC190332
0.872	High Similarity	NPC476002
0.8712	High Similarity	NPC320104
0.869	High Similarity	NPC237044
0.8688	High Similarity	NPC78733
0.8683	High Similarity	NPC2314
0.8675	High Similarity	NPC311991
0.8639	High Similarity	NPC474325
0.8631	High Similarity	NPC304675
0.8588	High Similarity	NPC474745
0.8563	High Similarity	NPC75958
0.8545	High Similarity	NPC180306
0.8529	High Similarity	NPC15919
0.8528	High Similarity	NPC92191
0.8528	High Similarity	NPC59028
0.8506	High Similarity	NPC141440
0.8497	Intermediate Similarity	NPC9867
0.8443	Intermediate Similarity	NPC474324
0.8443	Intermediate Similarity	NPC57812
0.8439	Intermediate Similarity	NPC475981
0.8439	Intermediate Similarity	NPC474746
0.8412	Intermediate Similarity	NPC49353
0.8405	Intermediate Similarity	NPC147091
0.8402	Intermediate Similarity	NPC65403
0.8393	Intermediate Similarity	NPC475845
0.8343	Intermediate Similarity	NPC230098
0.8343	Intermediate Similarity	NPC474708
0.8333	Intermediate Similarity	NPC156576
0.8314	Intermediate Similarity	NPC148693
0.8314	Intermediate Similarity	NPC294790
0.8314	Intermediate Similarity	NPC118633
0.8304	Intermediate Similarity	NPC187678
0.8294	Intermediate Similarity	NPC57272
0.8276	Intermediate Similarity	NPC248642
0.8253	Intermediate Similarity	NPC165797
0.8253	Intermediate Similarity	NPC205167
0.8253	Intermediate Similarity	NPC249274
0.8221	Intermediate Similarity	NPC148898
0.8167	Intermediate Similarity	NPC33256
0.8166	Intermediate Similarity	NPC124657
0.8161	Intermediate Similarity	NPC126284
0.8129	Intermediate Similarity	NPC474953
0.8118	Intermediate Similarity	NPC150879
0.8118	Intermediate Similarity	NPC301189
0.8118	Intermediate Similarity	NPC298186
0.8098	Intermediate Similarity	NPC274026
0.8086	Intermediate Similarity	NPC475959
0.8084	Intermediate Similarity	NPC69360
0.8072	Intermediate Similarity	NPC323443
0.8072	Intermediate Similarity	NPC180756
0.8024	Intermediate Similarity	NPC148014
0.8024	Intermediate Similarity	NPC40389
0.8024	Intermediate Similarity	NPC78359
0.8024	Intermediate Similarity	NPC65490
0.8024	Intermediate Similarity	NPC315707
0.8	Intermediate Similarity	NPC238530
0.8	Intermediate Similarity	NPC233029
0.8	Intermediate Similarity	NPC223124
0.8	Intermediate Similarity	NPC232514
0.8	Intermediate Similarity	NPC276944
0.8	Intermediate Similarity	NPC210148
0.7976	Intermediate Similarity	NPC111485
0.7966	Intermediate Similarity	NPC275132
0.7966	Intermediate Similarity	NPC233718
0.7964	Intermediate Similarity	NPC31311
0.7964	Intermediate Similarity	NPC234392
0.7956	Intermediate Similarity	NPC94499
0.7941	Intermediate Similarity	NPC233650
0.7933	Intermediate Similarity	NPC214116
0.7904	Intermediate Similarity	NPC216459
0.7904	Intermediate Similarity	NPC138487
0.7904	Intermediate Similarity	NPC41178
0.7898	Intermediate Similarity	NPC114364
0.7898	Intermediate Similarity	NPC320223
0.7895	Intermediate Similarity	NPC231198
0.7895	Intermediate Similarity	NPC134858
0.7892	Intermediate Similarity	NPC82285
0.7892	Intermediate Similarity	NPC471073
0.7892	Intermediate Similarity	NPC133011
0.7892	Intermediate Similarity	NPC270811
0.7879	Intermediate Similarity	NPC223125
0.787	Intermediate Similarity	NPC477080
0.7865	Intermediate Similarity	NPC102760
0.7861	Intermediate Similarity	NPC160570
0.7857	Intermediate Similarity	NPC160931
0.7857	Intermediate Similarity	NPC146288
0.7857	Intermediate Similarity	NPC37205
0.7848	Intermediate Similarity	NPC174191
0.7826	Intermediate Similarity	NPC474432
0.7826	Intermediate Similarity	NPC475713
0.7824	Intermediate Similarity	NPC18402
0.7818	Intermediate Similarity	NPC211296
0.7811	Intermediate Similarity	NPC129603
0.7809	Intermediate Similarity	NPC305847
0.7803	Intermediate Similarity	NPC210140
0.7803	Intermediate Similarity	NPC210918
0.7803	Intermediate Similarity	NPC247389
0.7796	Intermediate Similarity	NPC474427
0.7791	Intermediate Similarity	NPC130926
0.7791	Intermediate Similarity	NPC89199
0.7791	Intermediate Similarity	NPC185838
0.7791	Intermediate Similarity	NPC54125
0.7784	Intermediate Similarity	NPC128560
0.7784	Intermediate Similarity	NPC199465
0.7784	Intermediate Similarity	NPC229166
0.7778	Intermediate Similarity	NPC80472
0.7771	Intermediate Similarity	NPC219671
0.7771	Intermediate Similarity	NPC104077
0.7771	Intermediate Similarity	NPC147616
0.7771	Intermediate Similarity	NPC259742
0.7765	Intermediate Similarity	NPC476575
0.7765	Intermediate Similarity	NPC474650
0.7765	Intermediate Similarity	NPC302449
0.7759	Intermediate Similarity	NPC182257
0.7758	Intermediate Similarity	NPC428
0.7758	Intermediate Similarity	NPC24233
0.7758	Intermediate Similarity	NPC246587
0.7758	Intermediate Similarity	NPC147390
0.7758	Intermediate Similarity	NPC135538
0.7758	Intermediate Similarity	NPC476571
0.7753	Intermediate Similarity	NPC475794
0.7746	Intermediate Similarity	NPC329717
0.7746	Intermediate Similarity	NPC219341
0.7746	Intermediate Similarity	NPC198741
0.7746	Intermediate Similarity	NPC24264
0.7746	Intermediate Similarity	NPC476432
0.7737	Intermediate Similarity	NPC11708
0.7735	Intermediate Similarity	NPC162694
0.7733	Intermediate Similarity	NPC59567
0.7733	Intermediate Similarity	NPC293871
0.7733	Intermediate Similarity	NPC124433
0.773	Intermediate Similarity	NPC477898
0.7714	Intermediate Similarity	NPC329911
0.7709	Intermediate Similarity	NPC474607
0.7702	Intermediate Similarity	NPC156376
0.7701	Intermediate Similarity	NPC304846
0.7701	Intermediate Similarity	NPC298979
0.7697	Intermediate Similarity	NPC321505
0.7697	Intermediate Similarity	NPC476151
0.7697	Intermediate Similarity	NPC191376
0.7697	Intermediate Similarity	NPC179825
0.7692	Intermediate Similarity	NPC76079
0.7692	Intermediate Similarity	NPC237579
0.7688	Intermediate Similarity	NPC70290
0.7688	Intermediate Similarity	NPC73020
0.7688	Intermediate Similarity	NPC167546
0.7688	Intermediate Similarity	NPC14622
0.7688	Intermediate Similarity	NPC46744
0.7688	Intermediate Similarity	NPC193528
0.7688	Intermediate Similarity	NPC124302
0.7688	Intermediate Similarity	NPC76116
0.7688	Intermediate Similarity	NPC169743
0.7688	Intermediate Similarity	NPC302527
0.7688	Intermediate Similarity	NPC16805
0.7688	Intermediate Similarity	NPC215098
0.7688	Intermediate Similarity	NPC225774
0.7684	Intermediate Similarity	NPC329969
0.7683	Intermediate Similarity	NPC84181
0.7673	Intermediate Similarity	NPC11147
0.7669	Intermediate Similarity	NPC246947
0.7663	Intermediate Similarity	NPC117717
0.7654	Intermediate Similarity	NPC188163
0.7654	Intermediate Similarity	NPC149285
0.7654	Intermediate Similarity	NPC328750
0.7654	Intermediate Similarity	NPC213206
0.7654	Intermediate Similarity	NPC267408
0.7654	Intermediate Similarity	NPC474915
0.764	Intermediate Similarity	NPC35680
0.764	Intermediate Similarity	NPC241704
0.764	Intermediate Similarity	NPC283999
0.7636	Intermediate Similarity	NPC22150
0.7636	Intermediate Similarity	NPC18979
0.7636	Intermediate Similarity	NPC279298
0.7636	Intermediate Similarity	NPC38041
0.7625	Intermediate Similarity	NPC18576
0.7625	Intermediate Similarity	NPC7018
0.7625	Intermediate Similarity	NPC135777
0.7625	Intermediate Similarity	NPC142547
0.7624	Intermediate Similarity	NPC135772
0.7619	Intermediate Similarity	NPC286135

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 NPC252960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	605
0.2-0.3	1143
0.3-0.4	2482
0.4-0.5	2484
0.5-0.6	1464
0.6-0.7	668
0.7-0.8	129
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8397	Intermediate Similarity	NPD4236	Phase 3
0.8397	Intermediate Similarity	NPD4237	Approved
0.8293	Intermediate Similarity	NPD2978	Approved
0.8293	Intermediate Similarity	NPD2977	Approved
0.8225	Intermediate Similarity	NPD2970	Approved
0.8225	Intermediate Similarity	NPD2969	Approved
0.8182	Intermediate Similarity	NPD5772	Approved
0.8182	Intermediate Similarity	NPD5773	Approved
0.8176	Intermediate Similarity	NPD5241	Discontinued
0.807	Intermediate Similarity	NPD27	Approved
0.807	Intermediate Similarity	NPD2489	Approved
0.8059	Intermediate Similarity	NPD3051	Approved
0.8024	Intermediate Similarity	NPD2563	Approved
0.8024	Intermediate Similarity	NPD2560	Approved
0.8012	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4210	Discontinued
0.7953	Intermediate Similarity	NPD6071	Discontinued
0.795	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4663	Approved
0.7861	Intermediate Similarity	NPD4481	Phase 3
0.7857	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7906	Approved
0.7809	Intermediate Similarity	NPD7311	Approved
0.7809	Intermediate Similarity	NPD4577	Approved
0.7809	Intermediate Similarity	NPD7313	Approved
0.7809	Intermediate Similarity	NPD7312	Approved
0.7809	Intermediate Similarity	NPD4578	Approved
0.7809	Intermediate Similarity	NPD7310	Approved
0.7765	Intermediate Similarity	NPD7309	Approved
0.7738	Intermediate Similarity	NPD4772	Phase 2
0.7738	Intermediate Similarity	NPD4773	Phase 2
0.7716	Intermediate Similarity	NPD3060	Approved
0.7702	Intermediate Similarity	NPD1375	Discontinued
0.7697	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4420	Approved
0.7676	Intermediate Similarity	NPD5582	Discontinued
0.7665	Intermediate Similarity	NPD3687	Approved
0.7665	Intermediate Similarity	NPD3686	Approved
0.7654	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5006	Approved
0.7619	Intermediate Similarity	NPD5005	Approved
0.7609	Intermediate Similarity	NPD7296	Approved
0.758	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1753	Discontinued
0.75	Intermediate Similarity	NPD4162	Approved
0.7485	Intermediate Similarity	NPD4584	Approved
0.7484	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2973	Approved
0.7447	Intermediate Similarity	NPD2975	Approved
0.7447	Intermediate Similarity	NPD2974	Approved
0.7438	Intermediate Similarity	NPD2238	Phase 2
0.7414	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4005	Discontinued
0.741	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2677	Approved
0.741	Intermediate Similarity	NPD3692	Discontinued
0.7403	Intermediate Similarity	NPD3705	Approved
0.7386	Intermediate Similarity	NPD6107	Approved
0.7382	Intermediate Similarity	NPD2494	Approved
0.7382	Intermediate Similarity	NPD2493	Approved
0.7381	Intermediate Similarity	NPD4123	Phase 3
0.736	Intermediate Similarity	NPD2898	Approved
0.7337	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD52	Approved
0.7337	Intermediate Similarity	NPD7526	Approved
0.7333	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4580	Approved
0.7322	Intermediate Similarity	NPD7281	Phase 3
0.7322	Intermediate Similarity	NPD7280	Phase 3
0.7314	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7833	Phase 2
0.7314	Intermediate Similarity	NPD7831	Phase 2
0.7301	Intermediate Similarity	NPD6895	Approved
0.7301	Intermediate Similarity	NPD6896	Approved
0.7296	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3452	Approved
0.7292	Intermediate Similarity	NPD3450	Approved
0.7289	Intermediate Similarity	NPD5177	Phase 3
0.7283	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2490	Approved
0.7273	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2488	Approved
0.7268	Intermediate Similarity	NPD4583	Approved
0.7268	Intermediate Similarity	NPD4582	Approved
0.7262	Intermediate Similarity	NPD7124	Phase 2
0.7256	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7007	Discovery
0.7239	Intermediate Similarity	NPD823	Approved
0.7239	Intermediate Similarity	NPD817	Approved
0.7238	Intermediate Similarity	NPD6042	Phase 2
0.7238	Intermediate Similarity	NPD42	Phase 2
0.7232	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7037	Approved
0.7228	Intermediate Similarity	NPD2968	Approved
0.7228	Intermediate Similarity	NPD2971	Approved
0.7219	Intermediate Similarity	NPD1774	Approved
0.7216	Intermediate Similarity	NPD4002	Approved
0.7216	Intermediate Similarity	NPD5604	Discontinued
0.7216	Intermediate Similarity	NPD4004	Approved
0.7208	Intermediate Similarity	NPD1357	Approved
0.7205	Intermediate Similarity	NPD5718	Phase 2
0.7193	Intermediate Similarity	NPD2122	Discontinued
0.7193	Intermediate Similarity	NPD4727	Phase 1
0.7189	Intermediate Similarity	NPD8054	Approved
0.7189	Intermediate Similarity	NPD8053	Approved
0.7176	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5709	Phase 3
0.7168	Intermediate Similarity	NPD4678	Approved
0.7168	Intermediate Similarity	NPD4675	Approved
0.7164	Intermediate Similarity	NPD7047	Phase 3
0.716	Intermediate Similarity	NPD1132	Approved
0.716	Intermediate Similarity	NPD3122	Phase 3
0.716	Intermediate Similarity	NPD1136	Approved
0.716	Intermediate Similarity	NPD1130	Approved
0.7143	Intermediate Similarity	NPD8156	Discontinued
0.7135	Intermediate Similarity	NPD4666	Phase 3
0.7134	Intermediate Similarity	NPD3052	Approved
0.7134	Intermediate Similarity	NPD3054	Approved
0.712	Intermediate Similarity	NPD7039	Approved
0.712	Intermediate Similarity	NPD7038	Approved
0.7112	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4017	Approved
0.7108	Intermediate Similarity	NPD2161	Phase 2
0.7107	Intermediate Similarity	NPD4103	Phase 2
0.7107	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD598	Approved
0.7099	Intermediate Similarity	NPD601	Approved
0.7099	Intermediate Similarity	NPD597	Approved
0.7097	Intermediate Similarity	NPD6851	Approved
0.7097	Intermediate Similarity	NPD6853	Approved
0.7093	Intermediate Similarity	NPD3639	Approved
0.7093	Intermediate Similarity	NPD6030	Approved
0.7093	Intermediate Similarity	NPD6031	Approved
0.7093	Intermediate Similarity	NPD3641	Approved
0.7093	Intermediate Similarity	NPD3640	Phase 3
0.7088	Intermediate Similarity	NPD8099	Discontinued
0.7088	Intermediate Similarity	NPD8252	Approved
0.7088	Intermediate Similarity	NPD8251	Approved
0.7086	Intermediate Similarity	NPD3384	Approved
0.7086	Intermediate Similarity	NPD3382	Approved
0.7086	Intermediate Similarity	NPD3383	Approved
0.7077	Intermediate Similarity	NPD3057	Approved
0.7074	Intermediate Similarity	NPD6841	Approved
0.7074	Intermediate Similarity	NPD6843	Phase 3
0.7074	Intermediate Similarity	NPD6842	Approved
0.7062	Intermediate Similarity	NPD4965	Approved
0.7062	Intermediate Similarity	NPD4967	Phase 2
0.7062	Intermediate Similarity	NPD4966	Approved
0.7059	Intermediate Similarity	NPD6667	Approved
0.7059	Intermediate Similarity	NPD6666	Approved
0.7056	Intermediate Similarity	NPD4010	Discontinued
0.705	Intermediate Similarity	NPD5676	Approved
0.7048	Intermediate Similarity	NPD4108	Discontinued
0.7043	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6331	Phase 2
0.7041	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3179	Approved
0.7037	Intermediate Similarity	NPD3180	Approved
0.7035	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2492	Phase 1
0.7029	Intermediate Similarity	NPD6072	Discontinued
0.7025	Intermediate Similarity	NPD2232	Approved
0.7025	Intermediate Similarity	NPD2233	Approved
0.7025	Intermediate Similarity	NPD2230	Approved
0.7015	Intermediate Similarity	NPD7827	Phase 1
0.7012	Intermediate Similarity	NPD3109	Approved
0.7012	Intermediate Similarity	NPD3110	Approved
0.7012	Intermediate Similarity	NPD3061	Approved
0.7012	Intermediate Similarity	NPD3062	Approved
0.7012	Intermediate Similarity	NPD3059	Approved
0.7005	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5976	Discontinued
0.699	Remote Similarity	NPD3533	Approved
0.699	Remote Similarity	NPD2972	Approved
0.6989	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7298	Approved
0.6988	Remote Similarity	NPD6111	Discontinued
0.6982	Remote Similarity	NPD6674	Discontinued
0.6981	Remote Similarity	NPD4659	Approved
0.6978	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3536	Discontinued
0.6977	Remote Similarity	NPD3158	Phase 1
0.6977	Remote Similarity	NPD7019	Approved
0.6977	Remote Similarity	NPD7020	Approved
0.6977	Remote Similarity	NPD3157	Approved
0.6977	Remote Similarity	NPD4739	Approved
0.6973	Remote Similarity	NPD6297	Approved
0.697	Remote Similarity	NPD7999	Approved
0.6957	Remote Similarity	NPD6997	Phase 2
0.6957	Remote Similarity	NPD5313	Approved
0.6957	Remote Similarity	NPD5096	Phase 3
0.6957	Remote Similarity	NPD6584	Phase 3
0.6957	Remote Similarity	NPD5095	Phase 3
0.6957	Remote Similarity	NPD5312	Approved
0.6951	Remote Similarity	NPD3531	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