NPASS Compound

Structure

CID319549 OpenBabel06191716142D 39 43 0 0 1 0 0 0 0 0999 V2000 3.0692 7.9596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8999 7.4983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5856 3.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0770 7.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7909 6.0306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1429 1.0928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3768 -1.0980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9374 6.5065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2823 1.5558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8055 5.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9684 0.1312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4240 -0.8805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9872 -0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9872 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0772 1.7194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6264 4.8899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3374 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1409 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1409 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8335 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8335 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5658 2.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1023 5.7434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3768 1.0980 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4644 2.0713 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.2887 3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9227 7.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4240 0.8805 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.1277 4.0509 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 4.0795 5.7581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4352 4.0256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3987 8.3372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6289 3.2120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3483 3.4082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6011 6.5824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7630 -0.7906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7630 0.7906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3033 2.5725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 3 35 1 0 0 0 0 4 36 1 0 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 18 1 0 0 0 0 8 27 1 0 0 0 0 9 28 1 0 0 0 0 10 29 1 0 0 0 0 11 30 1 0 0 0 0 12 30 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 15 28 1 0 0 0 0 16 23 1 0 0 0 0 16 29 1 0 0 0 0 17 37 1 0 0 0 0 17 38 1 0 0 0 0 18 19 1 0 0 0 0 19 24 1 0 0 0 0 20 21 2 0 0 0 0 20 37 1 0 0 0 0 21 38 1 0 0 0 0 22 25 1 0 0 0 0 22 35 1 0 0 0 0 23 31 2 0 0 0 0 23 36 1 0 0 0 0 24 25 1 0 0 0 0 24 28 1 0 0 0 0 25 39 1 0 0 0 0 26 29 1 0 0 0 0 26 32 2 0 0 0 0 26 39 1 0 0 0 0 27 33 1 0 0 0 0 28 30 1 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	545.26
Volume:	541.648
LogP:	2.638
LogD:	2.823
LogS:	-4.65
# Rotatable Bonds:	11
TPSA:	123.99
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	4.98
Fsp3:	0.655
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:	-4.919
MDCK Permeability:	3.721252869581804e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.535
30% Bioavailability (F30%):	0.835

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.629
Plasma Protein Binding (PPB):	47.91353225708008%
Volume Distribution (VD):	1.42
Pgp-substrate:	42.497257232666016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.675
CYP2C19-inhibitor:	0.109
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.249
CYP2C9-substrate:	0.321
CYP2D6-inhibitor:	0.816
CYP2D6-substrate:	0.262
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	9.586
Half-life (T1/2):	0.1

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.647
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.024
Carcinogencity:	0.741
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.075

Download Data

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

Natural Product: NPC319549

Natural Product ID:	NPC319549
*Common Name:**	HYFHYPWGAURHIV-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HYFHYPWGAURHIV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H39NO9/c1-27(2,33)8-5-10-29(34,16-23(31)36-4)26(32)39-25-22(35-3)15-28-9-6-11-30(28)12-7-18-13-20-21(38-17-37-20)14-19(18)24(25)28/h13-15,24-25,33-34H,5-12,16-17H2,1-4H3
SMILES:	CC(C)(CCCC(CC(=O)OC)(C(=O)OC1C2C3=CC4=C(C=C3CCN5C2(CCC5)C=C1OC)OCO4)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL175858
PubChem CID:	3628
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003778] Cephalotaxus 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
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29182349]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	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
AC50	1
Potency	18

Activity Type	# Activity
Individual Protein	10
NON-MOLECULAR	4
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	158.5	nM	PMID[451731]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	3162.3	nM	PMID[451731]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	7.9	nM	PMID[451731]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	3548.1	nM	PMID[451731]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	12589.3	nM	PMID[451731]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	12589.25	nM	PMID[451731]
NPT445	Individual Protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	89.1	nM	PMID[451731]
NPT445	Individual Protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	6.4	nM	PMID[451731]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	37.6	nM	PMID[451731]
NPT2	Others	Unspecified		Potency	=	39.8	nM	PMID[451731]
NPT2	Others	Unspecified		Potency	=	562.3	nM	PMID[451731]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	6.7	nM	PMID[451731]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9.5	nM	PMID[451731]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	2983.0	nM	PMID[451731]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	16774.4	nM	PMID[451731]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	421.4	nM	PMID[451731]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	23694.5	nM	PMID[451731]
NPT2	Others	Unspecified		Potency	n.a.	1122.0	nM	PMID[451731]

☑ 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 NPC319549 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	249
0.1-0.2	1068
0.2-0.3	3367
0.3-0.4	9153
0.4-0.5	10287
0.5-0.6	11831
0.6-0.7	6205
0.7-0.8	502
0.8-0.85	28
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC165797
0.8315	Intermediate Similarity	NPC230098
0.8306	Intermediate Similarity	NPC474746
0.8306	Intermediate Similarity	NPC475981
0.8202	Intermediate Similarity	NPC301189
0.8202	Intermediate Similarity	NPC298186
0.8167	Intermediate Similarity	NPC57272
0.8148	Intermediate Similarity	NPC33256
0.8146	Intermediate Similarity	NPC476002
0.8142	Intermediate Similarity	NPC474745
0.8087	Intermediate Similarity	NPC474325
0.8077	Intermediate Similarity	NPC304675
0.8051	Intermediate Similarity	NPC80472
0.8033	Intermediate Similarity	NPC237044
0.8011	Intermediate Similarity	NPC474708
0.7956	Intermediate Similarity	NPC475845
0.7947	Intermediate Similarity	NPC94499
0.7901	Intermediate Similarity	NPC57812
0.7901	Intermediate Similarity	NPC474324
0.7838	Intermediate Similarity	NPC474470
0.7806	Intermediate Similarity	NPC286135
0.7802	Intermediate Similarity	NPC100566
0.7737	Intermediate Similarity	NPC162694
0.7735	Intermediate Similarity	NPC218614
0.7732	Intermediate Similarity	NPC474432
0.7732	Intermediate Similarity	NPC475713
0.7722	Intermediate Similarity	NPC4304
0.7705	Intermediate Similarity	NPC181653
0.7705	Intermediate Similarity	NPC190332
0.7704	Intermediate Similarity	NPC226652
0.7704	Intermediate Similarity	NPC120671
0.7704	Intermediate Similarity	NPC314100
0.7704	Intermediate Similarity	NPC72788
0.7696	Intermediate Similarity	NPC141440
0.7692	Intermediate Similarity	NPC215098
0.7692	Intermediate Similarity	NPC70290
0.7692	Intermediate Similarity	NPC73020
0.7692	Intermediate Similarity	NPC14622
0.7692	Intermediate Similarity	NPC46744
0.7692	Intermediate Similarity	NPC124302
0.765	Intermediate Similarity	NPC258128
0.7647	Intermediate Similarity	NPC35680
0.7638	Intermediate Similarity	NPC169605
0.7637	Intermediate Similarity	NPC320104
0.7626	Intermediate Similarity	NPC328700
0.7626	Intermediate Similarity	NPC119818
0.7626	Intermediate Similarity	NPC2173
0.7626	Intermediate Similarity	NPC202771
0.7617	Intermediate Similarity	NPC226708
0.7614	Intermediate Similarity	NPC474427
0.7609	Intermediate Similarity	NPC252960
0.7594	Intermediate Similarity	NPC49353
0.7592	Intermediate Similarity	NPC18306
0.7582	Intermediate Similarity	NPC76211
0.7581	Intermediate Similarity	NPC225597
0.7581	Intermediate Similarity	NPC477640
0.7581	Intermediate Similarity	NPC470739
0.7568	Intermediate Similarity	NPC290759
0.7568	Intermediate Similarity	NPC158148
0.7568	Intermediate Similarity	NPC82533
0.7568	Intermediate Similarity	NPC266176
0.7527	Intermediate Similarity	NPC311991
0.7527	Intermediate Similarity	NPC474953
0.7527	Intermediate Similarity	NPC474475
0.7514	Intermediate Similarity	NPC186316
0.7513	Intermediate Similarity	NPC15919
0.75	Intermediate Similarity	NPC187678
0.75	Intermediate Similarity	NPC180306
0.75	Intermediate Similarity	NPC235698
0.7486	Intermediate Similarity	NPC164082
0.7473	Intermediate Similarity	NPC475686
0.7473	Intermediate Similarity	NPC58766
0.7472	Intermediate Similarity	NPC477698
0.7459	Intermediate Similarity	NPC136757
0.745	Intermediate Similarity	NPC475747
0.7444	Intermediate Similarity	NPC56184
0.7444	Intermediate Similarity	NPC477699
0.7442	Intermediate Similarity	NPC14022
0.7419	Intermediate Similarity	NPC284842
0.7418	Intermediate Similarity	NPC38699
0.7411	Intermediate Similarity	NPC470646
0.7401	Intermediate Similarity	NPC3982
0.7394	Intermediate Similarity	NPC65403
0.7387	Intermediate Similarity	NPC267414
0.7385	Intermediate Similarity	NPC470642
0.7382	Intermediate Similarity	NPC99179
0.7382	Intermediate Similarity	NPC244554
0.7377	Intermediate Similarity	NPC478055
0.7377	Intermediate Similarity	NPC163635
0.7356	Intermediate Similarity	NPC147379
0.7345	Intermediate Similarity	NPC223185
0.7344	Intermediate Similarity	NPC474607
0.734	Intermediate Similarity	NPC75958
0.7337	Intermediate Similarity	NPC215829
0.7337	Intermediate Similarity	NPC97072
0.7333	Intermediate Similarity	NPC229882
0.7333	Intermediate Similarity	NPC166979
0.7333	Intermediate Similarity	NPC158635
0.733	Intermediate Similarity	NPC148693
0.733	Intermediate Similarity	NPC294790
0.733	Intermediate Similarity	NPC118633
0.7324	Intermediate Similarity	NPC475624
0.7323	Intermediate Similarity	NPC125924
0.732	Intermediate Similarity	NPC9867
0.7312	Intermediate Similarity	NPC152424
0.7312	Intermediate Similarity	NPC35345
0.7312	Intermediate Similarity	NPC100465
0.7308	Intermediate Similarity	NPC78733
0.7306	Intermediate Similarity	NPC102760
0.7306	Intermediate Similarity	NPC474650
0.7302	Intermediate Similarity	NPC477115
0.7293	Intermediate Similarity	NPC148898
0.7293	Intermediate Similarity	NPC223124
0.7292	Intermediate Similarity	NPC149285
0.7292	Intermediate Similarity	NPC475794
0.7288	Intermediate Similarity	NPC27159
0.7288	Intermediate Similarity	NPC15743
0.7283	Intermediate Similarity	NPC32373
0.7283	Intermediate Similarity	NPC237946
0.7283	Intermediate Similarity	NPC29727
0.7278	Intermediate Similarity	NPC293757
0.7278	Intermediate Similarity	NPC668
0.7278	Intermediate Similarity	NPC474965
0.7278	Intermediate Similarity	NPC174512
0.7278	Intermediate Similarity	NPC125570
0.7278	Intermediate Similarity	NPC477695
0.7273	Intermediate Similarity	NPC469815
0.7273	Intermediate Similarity	NPC469816
0.7263	Intermediate Similarity	NPC2314
0.7259	Intermediate Similarity	NPC63152
0.7258	Intermediate Similarity	NPC91634
0.7258	Intermediate Similarity	NPC268718
0.7258	Intermediate Similarity	NPC150943
0.7258	Intermediate Similarity	NPC96593
0.7243	Intermediate Similarity	NPC249274
0.7243	Intermediate Similarity	NPC19947
0.7243	Intermediate Similarity	NPC205167
0.7243	Intermediate Similarity	NPC207584
0.7231	Intermediate Similarity	NPC34780
0.7228	Intermediate Similarity	NPC254163
0.7228	Intermediate Similarity	NPC40389
0.7228	Intermediate Similarity	NPC78359
0.7228	Intermediate Similarity	NPC65490
0.7228	Intermediate Similarity	NPC129603
0.7228	Intermediate Similarity	NPC148014
0.7228	Intermediate Similarity	NPC315707
0.722	Intermediate Similarity	NPC11708
0.7219	Intermediate Similarity	NPC115624
0.7219	Intermediate Similarity	NPC231198
0.7219	Intermediate Similarity	NPC288149
0.7219	Intermediate Similarity	NPC247972
0.7213	Intermediate Similarity	NPC61604
0.7213	Intermediate Similarity	NPC245615
0.7213	Intermediate Similarity	NPC115466
0.7213	Intermediate Similarity	NPC299706
0.7204	Intermediate Similarity	NPC469654
0.7204	Intermediate Similarity	NPC469384
0.7204	Intermediate Similarity	NPC469479
0.7202	Intermediate Similarity	NPC27887
0.7202	Intermediate Similarity	NPC475244
0.72	Intermediate Similarity	NPC66909
0.7198	Intermediate Similarity	NPC303519
0.7198	Intermediate Similarity	NPC477700
0.7198	Intermediate Similarity	NPC13985
0.7198	Intermediate Similarity	NPC210642
0.7196	Intermediate Similarity	NPC475349
0.7196	Intermediate Similarity	NPC475442
0.7196	Intermediate Similarity	NPC475565
0.7196	Intermediate Similarity	NPC86469
0.7196	Intermediate Similarity	NPC475292
0.7196	Intermediate Similarity	NPC222531
0.7196	Intermediate Similarity	NPC474647
0.7191	Intermediate Similarity	NPC92693
0.7191	Intermediate Similarity	NPC218841
0.7189	Intermediate Similarity	NPC59028
0.7189	Intermediate Similarity	NPC92191
0.7184	Intermediate Similarity	NPC209229
0.7182	Intermediate Similarity	NPC216223
0.7182	Intermediate Similarity	NPC223125
0.7182	Intermediate Similarity	NPC145569
0.7175	Intermediate Similarity	NPC253722
0.7175	Intermediate Similarity	NPC40237
0.7175	Intermediate Similarity	NPC31751
0.7175	Intermediate Similarity	NPC151423
0.7175	Intermediate Similarity	NPC253481
0.7174	Intermediate Similarity	NPC30009
0.7174	Intermediate Similarity	NPC103197
0.7171	Intermediate Similarity	NPC476500
0.7166	Intermediate Similarity	NPC239818
0.7166	Intermediate Similarity	NPC119910
0.7166	Intermediate Similarity	NPC218471
0.7166	Intermediate Similarity	NPC59567
0.7165	Intermediate Similarity	NPC473562
0.7158	Intermediate Similarity	NPC306475
0.7151	Intermediate Similarity	NPC26353
0.7151	Intermediate Similarity	NPC163527
0.7151	Intermediate Similarity	NPC223335
0.7151	Intermediate Similarity	NPC18402
0.7151	Intermediate Similarity	NPC115281
0.7151	Intermediate Similarity	NPC40920

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 NPC319549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	551
0.2-0.3	1365
0.3-0.4	2539
0.4-0.5	2444
0.5-0.6	1483
0.6-0.7	548
0.7-0.8	49
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7296	Approved
0.7861	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4420	Approved
0.7626	Intermediate Similarity	NPD5006	Approved
0.7626	Intermediate Similarity	NPD5005	Approved
0.7619	Intermediate Similarity	NPD7280	Phase 3
0.7619	Intermediate Similarity	NPD7281	Phase 3
0.7475	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7827	Phase 1
0.7354	Intermediate Similarity	NPD5313	Approved
0.7354	Intermediate Similarity	NPD5312	Approved
0.7297	Intermediate Similarity	NPD6234	Discontinued
0.7283	Intermediate Similarity	NPD4965	Approved
0.7283	Intermediate Similarity	NPD4967	Phase 2
0.7283	Intermediate Similarity	NPD4966	Approved
0.7278	Intermediate Similarity	NPD4210	Discontinued
0.7228	Intermediate Similarity	NPD2560	Approved
0.7228	Intermediate Similarity	NPD2563	Approved
0.72	Intermediate Similarity	NPD2975	Approved
0.72	Intermediate Similarity	NPD2973	Approved
0.72	Intermediate Similarity	NPD2974	Approved
0.7178	Intermediate Similarity	NPD4580	Approved
0.7158	Intermediate Similarity	NPD6385	Approved
0.7158	Intermediate Similarity	NPD6386	Approved
0.7143	Intermediate Similarity	NPD2493	Approved
0.7143	Intermediate Similarity	NPD3452	Approved
0.7143	Intermediate Similarity	NPD2494	Approved
0.7143	Intermediate Similarity	NPD3450	Approved
0.7128	Intermediate Similarity	NPD6107	Approved
0.7122	Intermediate Similarity	NPD4583	Approved
0.7122	Intermediate Similarity	NPD4582	Approved
0.712	Intermediate Similarity	NPD7228	Approved
0.712	Intermediate Similarity	NPD37	Approved
0.7116	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6071	Discontinued
0.7073	Intermediate Similarity	NPD4004	Approved
0.7073	Intermediate Similarity	NPD4002	Approved
0.7039	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2490	Approved
0.7035	Intermediate Similarity	NPD2488	Approved
0.7033	Intermediate Similarity	NPD3641	Approved
0.7033	Intermediate Similarity	NPD3639	Approved
0.7033	Intermediate Similarity	NPD3640	Phase 3
0.7016	Intermediate Similarity	NPD4481	Phase 3
0.7011	Intermediate Similarity	NPD6876	Approved
0.7011	Intermediate Similarity	NPD6875	Approved
0.7005	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7315	Approved
0.699	Remote Similarity	NPD2968	Approved
0.699	Remote Similarity	NPD2971	Approved
0.6989	Remote Similarity	NPD2978	Approved
0.6989	Remote Similarity	NPD2977	Approved
0.6989	Remote Similarity	NPD7972	Discontinued
0.6974	Remote Similarity	NPD7240	Approved
0.6973	Remote Similarity	NPD4772	Phase 2
0.6973	Remote Similarity	NPD4773	Phase 2
0.6963	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7906	Approved
0.6927	Remote Similarity	NPD4236	Phase 3
0.6927	Remote Similarity	NPD4237	Approved
0.6923	Remote Similarity	NPD7999	Approved
0.6911	Remote Similarity	NPD3051	Approved
0.6904	Remote Similarity	NPD7312	Approved
0.6904	Remote Similarity	NPD7311	Approved
0.6904	Remote Similarity	NPD7310	Approved
0.6904	Remote Similarity	NPD7313	Approved
0.6902	Remote Similarity	NPD3687	Approved
0.6902	Remote Similarity	NPD3686	Approved
0.6901	Remote Similarity	NPD7930	Approved
0.6898	Remote Similarity	NPD5773	Approved
0.6898	Remote Similarity	NPD5772	Approved
0.6897	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7110	Phase 1
0.6882	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2969	Approved
0.6875	Remote Similarity	NPD5242	Approved
0.6875	Remote Similarity	NPD2970	Approved
0.6869	Remote Similarity	NPD6851	Approved
0.6869	Remote Similarity	NPD7309	Approved
0.6869	Remote Similarity	NPD6853	Approved
0.6866	Remote Similarity	NPD7907	Approved
0.6862	Remote Similarity	NPD5353	Approved
0.6859	Remote Similarity	NPD7199	Phase 2
0.685	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7497	Discontinued
0.6816	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD1375	Discontinued
0.6814	Remote Similarity	NPD5582	Discontinued
0.6802	Remote Similarity	NPD7038	Approved
0.6802	Remote Similarity	NPD7039	Approved
0.6786	Remote Similarity	NPD6723	Discontinued
0.6782	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7701	Phase 2
0.6766	Remote Similarity	NPD6842	Approved
0.6766	Remote Similarity	NPD6841	Approved
0.6766	Remote Similarity	NPD6843	Phase 3
0.6763	Remote Similarity	NPD4107	Approved
0.6754	Remote Similarity	NPD6315	Phase 2
0.6753	Remote Similarity	NPD2489	Approved
0.6753	Remote Similarity	NPD27	Approved
0.6751	Remote Similarity	NPD6297	Approved
0.6739	Remote Similarity	NPD3146	Approved
0.6739	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4577	Approved
0.6734	Remote Similarity	NPD4578	Approved
0.6721	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD4663	Approved
0.6715	Remote Similarity	NPD7565	Approved
0.6714	Remote Similarity	NPD4040	Phase 1
0.6714	Remote Similarity	NPD8320	Phase 1
0.6714	Remote Similarity	NPD8319	Approved
0.6712	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6625	Approved
0.6706	Remote Similarity	NPD3705	Approved
0.6702	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3057	Approved
0.6697	Remote Similarity	NPD4665	Approved
0.6697	Remote Similarity	NPD4111	Phase 1
0.6685	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6997	Phase 2
0.6682	Remote Similarity	NPD8404	Phase 2
0.6667	Remote Similarity	NPD5241	Discontinued
0.6667	Remote Similarity	NPD2238	Phase 2
0.6651	Remote Similarity	NPD4482	Phase 3
0.665	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7047	Phase 3
0.6632	Remote Similarity	NPD4585	Approved
0.663	Remote Similarity	NPD6667	Approved
0.663	Remote Similarity	NPD6666	Approved
0.6619	Remote Similarity	NPD2972	Approved
0.6619	Remote Similarity	NPD3533	Approved
0.6618	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5089	Approved
0.6614	Remote Similarity	NPD6873	Phase 2
0.6614	Remote Similarity	NPD5090	Approved
0.6613	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4110	Phase 3
0.6612	Remote Similarity	NPD2575	Approved
0.6612	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.661	Remote Similarity	NPD554	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6620	Discovery
0.6592	Remote Similarity	NPD2653	Approved
0.6578	Remote Similarity	NPD7427	Discontinued
0.6576	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4476	Approved
0.6575	Remote Similarity	NPD2161	Phase 2
0.6575	Remote Similarity	NPD6032	Approved
0.6575	Remote Similarity	NPD4477	Approved
0.6564	Remote Similarity	NPD4166	Phase 2
0.6559	Remote Similarity	NPD4584	Approved
0.6558	Remote Similarity	NPD7874	Approved
0.6558	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7685	Pre-registration
0.655	Remote Similarity	NPD7048	Phase 3
0.6546	Remote Similarity	NPD4666	Phase 3
0.6545	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4859	Phase 1
0.6541	Remote Similarity	NPD7124	Phase 2
0.654	Remote Similarity	NPD3448	Approved
0.654	Remote Similarity	NPD2491	Approved
0.6535	Remote Similarity	NPD8054	Approved
0.6535	Remote Similarity	NPD8053	Approved
0.6534	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7831	Phase 2
0.6528	Remote Similarity	NPD7833	Phase 2
0.6528	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6776	Approved
0.6524	Remote Similarity	NPD7526	Approved
0.6524	Remote Similarity	NPD52	Approved
0.6524	Remote Similarity	NPD6780	Approved
0.6524	Remote Similarity	NPD6778	Approved
0.6524	Remote Similarity	NPD6779	Approved
0.6524	Remote Similarity	NPD6782	Approved
0.6524	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6781	Approved
0.6524	Remote Similarity	NPD6777	Approved
0.6517	Remote Similarity	NPD7549	Discontinued
0.6517	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5978	Approved
0.651	Remote Similarity	NPD5977	Approved
0.6509	Remote Similarity	NPD7435	Discontinued
0.6508	Remote Similarity	NPD824	Approved
0.6495	Remote Similarity	NPD5709	Phase 3
0.6492	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7248	Discontinued
0.6486	Remote Similarity	NPD2677	Approved
0.6484	Remote Similarity	NPD2240	Approved
0.6484	Remote Similarity	NPD2239	Approved
0.6484	Remote Similarity	NPD9570	Approved
0.6482	Remote Similarity	NPD8156	Discontinued
0.648	Remote Similarity	NPD5710	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