NPASS Compound

Structure

CID313670 OpenBabel06191716122D 46 46 0 0 1 0 0 0 0 0999 V2000 -6.3404 -1.6901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4079 -9.0656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1120 0.9937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3411 -1.6527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8738 -0.7686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9376 -3.9376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9376 -4.9376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7151 -2.9627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7151 -5.9126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2812 -2.0617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8745 -0.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2812 -6.8135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6577 -1.2799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6577 -7.5954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8759 -0.6564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4072 0.1529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6577 -7.5954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7151 -5.9126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -8.6527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9376 -3.9376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -8.8752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2812 -2.0617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8759 -8.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2812 -6.8135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8759 -8.2188 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9376 -4.9376 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -8.8752 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7151 -2.9627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9749 -0.2225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4079 0.1903 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9749 -8.6527 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6577 -1.2799 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8759 -0.6564 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1279 -7.3456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4079 -9.0656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9313 -5.0496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1120 -9.8690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6590 -2.6324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3052 0.7214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9407 1.0744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3052 -9.5966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3648 -0.5728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3052 0.7214 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 4 1 0 0 0 0 2 23 1 0 0 0 0 4 5 1 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 12 2 0 0 0 0 10 13 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 23 2 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 25 1 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 19 26 1 0 0 0 0 19 28 1 0 0 0 0 20 27 1 0 0 0 0 20 29 1 0 0 0 0 21 28 1 0 0 0 0 21 32 1 0 0 0 0 22 29 1 0 0 0 0 22 33 1 0 0 0 0 23 32 1 0 0 0 0 24 3 1 6 0 0 0 24 30 1 0 0 0 0 24 46 1 0 0 0 0 25 36 1 6 0 0 0 26 37 1 6 0 0 0 27 38 1 6 0 0 0 28 39 1 6 0 0 0 29 40 1 6 0 0 0 30 41 1 1 0 0 0 31 42 1 1 0 0 0 32 43 1 1 0 0 0 33 34 1 0 0 0 0 33 44 1 6 0 0 0 34 31 1 1 0 0 0 34 35 1 0 0 0 0 35 45 2 0 0 0 0 35 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.4
Volume:	686.233
LogP:	0.051
LogD:	0.036
LogS:	-3.369
# Rotatable Bonds:	5
TPSA:	208.37
# H-Bond Aceptor:	11
# H-Bond Donor:	9
# Rings:	1
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.154
Synthetic Accessibility Score:	5.847
Fsp3:	0.686
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.393
MDCK Permeability:	6.231510633369908e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.376
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.183
Plasma Protein Binding (PPB):	20.84196662902832%
Volume Distribution (VD):	0.44
Pgp-substrate:	5.778331279754639%

ADMET: Metabolism

CYP1A2-inhibitor:	0.332
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.994
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.163
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	1.463
Half-life (T1/2):	0.33

ADMET: Toxicity

hERG Blockers:	0.75
Human Hepatotoxicity (H-HT):	0.916
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.915
Carcinogencity:	0.337
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC313670

Natural Product ID:	NPC313670
*Common Name:**	Filipin
IUPAC Name:	(3R,4S,6S,8S,10R,12R,14R,16S,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,16,27-octahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
Synonyms:	Filipin; U-5956
Standard InCHIKey:	IMQSIXYSKPIGPD-YQRUMEKGSA-N
Standard InCHI:	InChI=1S/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14+/t24-,25+,26-,27+,28-,29+,30+,31-,32+,33+,34-/m1/s1
SMILES:	CCCCC[C@H]([C@@H]1[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@H](O)/C(=C/C=C/C=C/C=C/C=C/[C@@H]([C@H](OC1=O)C)O)/C)O
Synthetic Gene Cluster:	BGC0000059;
ChEMBL Identifier:	CHEMBL252059
PubChem CID:	6433194
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO4731	Streptomyces filipinensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[5453318]
NPO4731	Streptomyces filipinensis	Species	Streptomycetaceae	Bacteria	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
Others	12

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	3
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	23.0	mm	PMID[480030]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	>	5.0	mm	PMID[480031]
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	>	5.0	mm	PMID[480031]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	>	5.0	mm	PMID[480031]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	>	5.0	mm	PMID[480031]
NPT2792	Organism	Penicillium digitatum	Penicillium digitatum	IZ	=	29.0	mm	PMID[480032]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	21.0	mm	PMID[480032]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	15.0	mm	PMID[480033]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	93.93	%	PMID[480034]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	96.46	%	PMID[480034]

☑ 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 NPC313670 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	210
0.1-0.2	1108
0.2-0.3	4207
0.3-0.4	7401
0.4-0.5	16655
0.5-0.6	8771
0.6-0.7	3645
0.7-0.8	662
0.8-0.85	30
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC477959
0.9186	High Similarity	NPC86005
0.8791	High Similarity	NPC5418
0.8602	High Similarity	NPC165332
0.8602	High Similarity	NPC195645
0.8602	High Similarity	NPC180722
0.8444	Intermediate Similarity	NPC201046
0.8421	Intermediate Similarity	NPC161855
0.837	Intermediate Similarity	NPC472199
0.8316	Intermediate Similarity	NPC40812
0.8298	Intermediate Similarity	NPC36954
0.828	Intermediate Similarity	NPC478037
0.828	Intermediate Similarity	NPC478036
0.8261	Intermediate Similarity	NPC474761
0.8261	Intermediate Similarity	NPC476004
0.8222	Intermediate Similarity	NPC164393
0.8211	Intermediate Similarity	NPC473291
0.8191	Intermediate Similarity	NPC472198
0.8172	Intermediate Similarity	NPC472197
0.8163	Intermediate Similarity	NPC473596
0.8152	Intermediate Similarity	NPC118193
0.8152	Intermediate Similarity	NPC256902
0.8132	Intermediate Similarity	NPC179659
0.8119	Intermediate Similarity	NPC193765
0.8119	Intermediate Similarity	NPC473807
0.8111	Intermediate Similarity	NPC137033
0.81	Intermediate Similarity	NPC476738
0.81	Intermediate Similarity	NPC476740
0.809	Intermediate Similarity	NPC69469
0.8085	Intermediate Similarity	NPC475912
0.8085	Intermediate Similarity	NPC476300
0.8081	Intermediate Similarity	NPC309398
0.8065	Intermediate Similarity	NPC316228
0.8043	Intermediate Similarity	NPC227379
0.8043	Intermediate Similarity	NPC153805
0.8043	Intermediate Similarity	NPC474471
0.8041	Intermediate Similarity	NPC308567
0.8041	Intermediate Similarity	NPC261377
0.8041	Intermediate Similarity	NPC83895
0.8041	Intermediate Similarity	NPC187761
0.8041	Intermediate Similarity	NPC255592
0.8021	Intermediate Similarity	NPC476315
0.8	Intermediate Similarity	NPC469869
0.8	Intermediate Similarity	NPC474776
0.798	Intermediate Similarity	NPC472754
0.7979	Intermediate Similarity	NPC184463
0.7979	Intermediate Similarity	NPC30515
0.7976	Intermediate Similarity	NPC325627
0.7976	Intermediate Similarity	NPC326024
0.7959	Intermediate Similarity	NPC475053
0.7957	Intermediate Similarity	NPC474032
0.7935	Intermediate Similarity	NPC248602
0.7931	Intermediate Similarity	NPC11796
0.7931	Intermediate Similarity	NPC218817
0.7917	Intermediate Similarity	NPC14961
0.7917	Intermediate Similarity	NPC270013
0.7917	Intermediate Similarity	NPC107476
0.7917	Intermediate Similarity	NPC272050
0.7917	Intermediate Similarity	NPC471142
0.7912	Intermediate Similarity	NPC21469
0.7912	Intermediate Similarity	NPC475206
0.79	Intermediate Similarity	NPC473816
0.79	Intermediate Similarity	NPC472755
0.79	Intermediate Similarity	NPC475367
0.79	Intermediate Similarity	NPC474581
0.7889	Intermediate Similarity	NPC11620
0.7879	Intermediate Similarity	NPC472753
0.7872	Intermediate Similarity	NPC478003
0.7872	Intermediate Similarity	NPC478004
0.7872	Intermediate Similarity	NPC158388
0.7872	Intermediate Similarity	NPC51004
0.7865	Intermediate Similarity	NPC184208
0.7865	Intermediate Similarity	NPC8538
0.7865	Intermediate Similarity	NPC315731
0.7864	Intermediate Similarity	NPC313668
0.7864	Intermediate Similarity	NPC315836
0.7857	Intermediate Similarity	NPC475653
0.785	Intermediate Similarity	NPC475642
0.7835	Intermediate Similarity	NPC477921
0.7835	Intermediate Similarity	NPC473859
0.7835	Intermediate Similarity	NPC255410
0.7826	Intermediate Similarity	NPC316426
0.7826	Intermediate Similarity	NPC477993
0.7826	Intermediate Similarity	NPC477994
0.7826	Intermediate Similarity	NPC315395
0.7826	Intermediate Similarity	NPC122502
0.7822	Intermediate Similarity	NPC220964
0.7822	Intermediate Similarity	NPC475676
0.7812	Intermediate Similarity	NPC474035
0.7812	Intermediate Similarity	NPC81386
0.7802	Intermediate Similarity	NPC243618
0.7802	Intermediate Similarity	NPC151176
0.7802	Intermediate Similarity	NPC3464
0.7802	Intermediate Similarity	NPC475963
0.7802	Intermediate Similarity	NPC70424
0.78	Intermediate Similarity	NPC149371
0.7789	Intermediate Similarity	NPC473321
0.7778	Intermediate Similarity	NPC469870
0.7778	Intermediate Similarity	NPC288876
0.7778	Intermediate Similarity	NPC469871
0.7766	Intermediate Similarity	NPC307411
0.7766	Intermediate Similarity	NPC97577
0.7755	Intermediate Similarity	NPC120299
0.7753	Intermediate Similarity	NPC103634
0.7742	Intermediate Similarity	NPC474765
0.7738	Intermediate Similarity	NPC476660
0.7732	Intermediate Similarity	NPC477922
0.7732	Intermediate Similarity	NPC475659
0.7732	Intermediate Similarity	NPC300710
0.7727	Intermediate Similarity	NPC127526
0.7723	Intermediate Similarity	NPC4620
0.7723	Intermediate Similarity	NPC475871
0.7723	Intermediate Similarity	NPC475945
0.7717	Intermediate Similarity	NPC99395
0.7717	Intermediate Similarity	NPC197903
0.7714	Intermediate Similarity	NPC287311
0.7708	Intermediate Similarity	NPC476049
0.7708	Intermediate Similarity	NPC295204
0.7708	Intermediate Similarity	NPC273579
0.7708	Intermediate Similarity	NPC288240
0.7708	Intermediate Similarity	NPC320089
0.7708	Intermediate Similarity	NPC212486
0.7708	Intermediate Similarity	NPC162205
0.7708	Intermediate Similarity	NPC81419
0.7708	Intermediate Similarity	NPC179746
0.77	Intermediate Similarity	NPC474742
0.77	Intermediate Similarity	NPC316250
0.77	Intermediate Similarity	NPC47880
0.7692	Intermediate Similarity	NPC15218
0.7684	Intermediate Similarity	NPC473619
0.7684	Intermediate Similarity	NPC474232
0.7684	Intermediate Similarity	NPC473448
0.7677	Intermediate Similarity	NPC471144
0.766	Intermediate Similarity	NPC473715
0.766	Intermediate Similarity	NPC472008
0.766	Intermediate Similarity	NPC89001
0.766	Intermediate Similarity	NPC281516
0.766	Intermediate Similarity	NPC202672
0.7647	Intermediate Similarity	NPC472756
0.7647	Intermediate Similarity	NPC470104
0.7647	Intermediate Similarity	NPC100487
0.7647	Intermediate Similarity	NPC203659
0.7642	Intermediate Similarity	NPC66108
0.764	Intermediate Similarity	NPC471537
0.7634	Intermediate Similarity	NPC116575
0.7634	Intermediate Similarity	NPC309211
0.7634	Intermediate Similarity	NPC61527
0.7634	Intermediate Similarity	NPC475753
0.7634	Intermediate Similarity	NPC469483
0.7629	Intermediate Similarity	NPC303942
0.7629	Intermediate Similarity	NPC57405
0.7624	Intermediate Similarity	NPC474709
0.7624	Intermediate Similarity	NPC474747
0.7624	Intermediate Similarity	NPC478156
0.7624	Intermediate Similarity	NPC313569
0.7619	Intermediate Similarity	NPC473772
0.7609	Intermediate Similarity	NPC474780
0.7609	Intermediate Similarity	NPC9868
0.7604	Intermediate Similarity	NPC36491
0.7604	Intermediate Similarity	NPC12172
0.7604	Intermediate Similarity	NPC208886
0.76	Intermediate Similarity	NPC475949
0.7596	Intermediate Similarity	NPC474664
0.7596	Intermediate Similarity	NPC233379
0.7596	Intermediate Similarity	NPC14862
0.7596	Intermediate Similarity	NPC327286
0.7596	Intermediate Similarity	NPC169888
0.7596	Intermediate Similarity	NPC55972
0.7582	Intermediate Similarity	NPC477390
0.7582	Intermediate Similarity	NPC477385
0.7579	Intermediate Similarity	NPC477011
0.7579	Intermediate Similarity	NPC295312
0.7579	Intermediate Similarity	NPC477016
0.7579	Intermediate Similarity	NPC477017
0.7576	Intermediate Similarity	NPC245521
0.7573	Intermediate Similarity	NPC472749
0.7573	Intermediate Similarity	NPC472751
0.7568	Intermediate Similarity	NPC183353
0.7568	Intermediate Similarity	NPC469812
0.7568	Intermediate Similarity	NPC170880
0.7568	Intermediate Similarity	NPC156379
0.7568	Intermediate Similarity	NPC475383
0.7558	Intermediate Similarity	NPC477085
0.7556	Intermediate Similarity	NPC200446
0.7553	Intermediate Similarity	NPC471738
0.7551	Intermediate Similarity	NPC314009
0.7551	Intermediate Similarity	NPC54905
0.7551	Intermediate Similarity	NPC472469
0.7549	Intermediate Similarity	NPC69171
0.7549	Intermediate Similarity	NPC474165
0.7549	Intermediate Similarity	NPC110989
0.7547	Intermediate Similarity	NPC21713
0.7547	Intermediate Similarity	NPC475608
0.7528	Intermediate Similarity	NPC121200
0.7527	Intermediate Similarity	NPC100921
0.7527	Intermediate Similarity	NPC242233
0.7527	Intermediate Similarity	NPC477018
0.7527	Intermediate Similarity	NPC471494
0.7526	Intermediate Similarity	NPC238090
0.7526	Intermediate Similarity	NPC472195

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 NPC313670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1592
0.2-0.3	3586
0.3-0.4	2356
0.4-0.5	975
0.5-0.6	362
0.6-0.7	71
0.7-0.8	16
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9882	High Similarity	NPD7983	Approved
0.8602	High Similarity	NPD7839	Suspended
0.8478	Intermediate Similarity	NPD5778	Approved
0.8478	Intermediate Similarity	NPD5779	Approved
0.8065	Intermediate Similarity	NPD46	Approved
0.8065	Intermediate Similarity	NPD7838	Discovery
0.8065	Intermediate Similarity	NPD6698	Approved
0.7766	Intermediate Similarity	NPD6101	Approved
0.7766	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7154	Phase 3
0.7634	Intermediate Similarity	NPD5786	Approved
0.7604	Intermediate Similarity	NPD6411	Approved
0.7568	Intermediate Similarity	NPD8513	Phase 3
0.7568	Intermediate Similarity	NPD8516	Approved
0.7568	Intermediate Similarity	NPD8515	Approved
0.7568	Intermediate Similarity	NPD8517	Approved
0.75	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7637	Suspended
0.7391	Intermediate Similarity	NPD4269	Approved
0.7391	Intermediate Similarity	NPD4270	Approved
0.7381	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5362	Discontinued
0.7257	Intermediate Similarity	NPD8444	Approved
0.7241	Intermediate Similarity	NPD8074	Phase 3
0.7222	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD8342	Approved
0.7217	Intermediate Similarity	NPD8340	Approved
0.7217	Intermediate Similarity	NPD8341	Approved
0.7217	Intermediate Similarity	NPD8299	Approved
0.7204	Intermediate Similarity	NPD6435	Approved
0.7188	Intermediate Similarity	NPD4251	Approved
0.7188	Intermediate Similarity	NPD4250	Approved
0.7174	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4252	Approved
0.7158	Intermediate Similarity	NPD5363	Approved
0.713	Intermediate Similarity	NPD6371	Approved
0.713	Intermediate Similarity	NPD7830	Approved
0.713	Intermediate Similarity	NPD7829	Approved
0.7097	Intermediate Similarity	NPD5369	Approved
0.7083	Intermediate Similarity	NPD4249	Approved
0.7009	Intermediate Similarity	NPD8273	Phase 1
0.7009	Intermediate Similarity	NPD8451	Approved
0.6989	Remote Similarity	NPD4821	Approved
0.6989	Remote Similarity	NPD4822	Approved
0.6989	Remote Similarity	NPD4819	Approved
0.6989	Remote Similarity	NPD4820	Approved
0.6989	Remote Similarity	NPD5368	Approved
0.6979	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5785	Approved
0.6957	Remote Similarity	NPD4268	Approved
0.6957	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4271	Approved
0.6949	Remote Similarity	NPD8448	Approved
0.6863	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7641	Discontinued
0.6813	Remote Similarity	NPD8039	Approved
0.6789	Remote Similarity	NPD6686	Approved
0.6777	Remote Similarity	NPD8390	Approved
0.6777	Remote Similarity	NPD8392	Approved
0.6777	Remote Similarity	NPD8391	Approved
0.6771	Remote Similarity	NPD5331	Approved
0.6771	Remote Similarity	NPD5332	Approved
0.6759	Remote Similarity	NPD5048	Discontinued
0.6737	Remote Similarity	NPD4790	Discontinued
0.67	Remote Similarity	NPD5370	Suspended
0.6698	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6421	Discontinued
0.6667	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4225	Approved
0.6628	Remote Similarity	NPD3197	Phase 1
0.6604	Remote Similarity	NPD6648	Approved
0.6598	Remote Similarity	NPD6110	Phase 1
0.6569	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7642	Approved
0.65	Remote Similarity	NPD7524	Approved
0.6486	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7115	Discovery
0.6466	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7500	Approved
0.6466	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5282	Discontinued
0.6441	Remote Similarity	NPD6319	Approved
0.6437	Remote Similarity	NPD7909	Approved
0.6417	Remote Similarity	NPD8328	Phase 3
0.6404	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD6422	Discontinued
0.6327	Remote Similarity	NPD5209	Approved
0.6316	Remote Similarity	NPD4756	Discovery
0.6316	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7639	Approved
0.6296	Remote Similarity	NPD7640	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6263	Remote Similarity	NPD6695	Phase 3
0.6261	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3732	Approved
0.6204	Remote Similarity	NPD7638	Approved
0.62	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD8080	Discontinued
0.6179	Remote Similarity	NPD7507	Approved
0.6176	Remote Similarity	NPD7750	Discontinued
0.6172	Remote Similarity	NPD8415	Approved
0.614	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7514	Phase 3
0.6122	Remote Similarity	NPD7332	Phase 2
0.6111	Remote Similarity	NPD7331	Phase 2
0.6106	Remote Similarity	NPD6412	Phase 2
0.6105	Remote Similarity	NPD8264	Approved
0.6102	Remote Similarity	NPD2629	Approved
0.6098	Remote Similarity	NPD7492	Approved
0.6082	Remote Similarity	NPD7145	Approved
0.608	Remote Similarity	NPD7736	Approved
0.6068	Remote Similarity	NPD4632	Approved
0.6063	Remote Similarity	NPD7260	Phase 2
0.6061	Remote Similarity	NPD6902	Approved
0.6058	Remote Similarity	NPD1695	Approved
0.6048	Remote Similarity	NPD6616	Approved
0.604	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6399	Phase 3
0.6033	Remote Similarity	NPD6054	Approved
0.602	Remote Similarity	NPD6929	Approved
0.6019	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7078	Approved
0.5984	Remote Similarity	NPD6921	Approved
0.5982	Remote Similarity	NPD6647	Phase 2
0.5981	Remote Similarity	NPD7748	Approved
0.5979	Remote Similarity	NPD5776	Phase 2
0.5979	Remote Similarity	NPD6925	Approved
0.5971	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6685	Approved
0.596	Remote Similarity	NPD6930	Phase 2
0.596	Remote Similarity	NPD6931	Approved
0.5952	Remote Similarity	NPD3194	Approved
0.5952	Remote Similarity	NPD3195	Phase 2
0.5952	Remote Similarity	NPD3196	Approved
0.5952	Remote Similarity	NPD3728	Approved
0.5952	Remote Similarity	NPD3730	Approved
0.5952	Remote Similarity	NPD4266	Approved
0.5935	Remote Similarity	NPD6370	Approved
0.5932	Remote Similarity	NPD8133	Approved
0.5917	Remote Similarity	NPD7505	Discontinued
0.5913	Remote Similarity	NPD6899	Approved
0.5913	Remote Similarity	NPD6881	Approved
0.5902	Remote Similarity	NPD6059	Approved
0.5897	Remote Similarity	NPD8130	Phase 1
0.5897	Remote Similarity	NPD6649	Approved
0.5897	Remote Similarity	NPD6650	Approved
0.5897	Remote Similarity	NPD1719	Phase 1
0.5895	Remote Similarity	NPD4732	Discontinued
0.5877	Remote Similarity	NPD6402	Approved
0.5877	Remote Similarity	NPD6675	Approved
0.5877	Remote Similarity	NPD5739	Approved
0.5877	Remote Similarity	NPD7128	Approved
0.5862	Remote Similarity	NPD6373	Approved
0.5862	Remote Similarity	NPD6372	Approved
0.5862	Remote Similarity	NPD6109	Phase 1
0.5854	Remote Similarity	NPD6016	Approved
0.5854	Remote Similarity	NPD8268	Approved
0.5854	Remote Similarity	NPD6015	Approved
0.5854	Remote Similarity	NPD8269	Approved
0.5854	Remote Similarity	NPD8267	Approved
0.5854	Remote Similarity	NPD8266	Approved
0.5854	Remote Similarity	NPD7503	Approved
0.5847	Remote Similarity	NPD6882	Approved
0.5842	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7345	Approved
0.5841	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3172	Approved
0.5826	Remote Similarity	NPD5697	Approved
0.5824	Remote Similarity	NPD7341	Phase 2
0.5824	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6084	Phase 2
0.5818	Remote Similarity	NPD6083	Phase 2
0.5818	Remote Similarity	NPD7902	Approved
0.5816	Remote Similarity	NPD6932	Approved
0.5812	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7102	Approved
0.5812	Remote Similarity	NPD7290	Approved
0.5812	Remote Similarity	NPD4634	Approved
0.5812	Remote Similarity	NPD6883	Approved
0.5806	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7623	Phase 3
0.5806	Remote Similarity	NPD5988	Approved
0.5794	Remote Similarity	NPD7087	Discontinued
0.5794	Remote Similarity	NPD7515	Phase 2
0.5785	Remote Similarity	NPD6009	Approved
0.5776	Remote Similarity	NPD7320	Approved
0.5772	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD9495	Approved
0.5763	Remote Similarity	NPD6869	Approved
0.5763	Remote Similarity	NPD6847	Approved
0.5763	Remote Similarity	NPD2204	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