NPASS Compound

Structure

CID131002 OpenBabel06191715492D 41 42 0 0 1 0 0 0 0 0999 V2000 7.9418 13.1761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8554 12.7694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9599 11.7748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8735 11.3681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9780 10.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8915 9.9668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9961 8.9723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9096 8.5656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0141 7.5711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2024 2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2024 2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7024 3.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9277 7.1643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7024 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7024 3.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0322 6.1698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7024 5.4128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2024 4.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7024 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2024 4.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7024 5.4128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9458 5.7631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2024 4.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2413 3.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2902 2.8717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2024 4.5468 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.0503 4.7685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.7024 3.6808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.2413 4.1808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.7024 3.6808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7024 3.6808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.9638 4.3618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2024 2.8147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 1.7213 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 12.2902 4.4898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 24 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 26 1 0 0 0 0 25 33 1 0 0 0 0 26 34 1 0 0 0 0 27 28 1 0 0 0 0 27 29 2 0 0 0 0 28 2 1 6 0 0 0 28 40 1 0 0 0 0 29 35 1 0 0 0 0 30 36 1 6 0 0 0 31 37 1 1 0 0 0 32 38 1 6 0 0 0 33 31 1 1 0 0 0 33 41 1 0 0 0 0 34 32 1 6 0 0 0 34 41 1 0 0 0 0 35 39 2 0 0 0 0 35 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.47
Volume:	644.271
LogP:	9.199
LogD:	4.783
LogS:	-6.679
# Rotatable Bonds:	26
TPSA:	103.29
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.082
Synthetic Accessibility Score:	4.296
Fsp3:	0.886
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:	-5.271
MDCK Permeability:	1.8935987100121565e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.821

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	97.82928466796875%
Volume Distribution (VD):	0.898
Pgp-substrate:	2.1251261234283447%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.201
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.131
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	4.563
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.224
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.603
Skin Sensitization:	0.972
Carcinogencity:	0.019
Eye Corrosion:	0.004
Eye Irritation:	0.052
Respiratory Toxicity:	0.189

Download Data

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

Natural Product: NPC131002

Natural Product ID:	NPC131002
*Common Name:**	Corossoline
IUPAC Name:	(2S)-4-[(8R,13R)-8,13-dihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms:	Corossoline
Standard InCHIKey:	GBNCDYGXXWZSAO-YZDQYAEISA-N
Standard InCHI:	InChI=1S/C35H64O6/c1-3-4-5-6-7-8-9-10-14-17-23-31(37)33-25-26-34(41-33)32(38)24-19-18-22-30(36)21-16-13-11-12-15-20-29-27-28(2)40-35(29)39/h27-28,30-34,36-38H,3-26H2,1-2H3/t28-,30+,31+,32+,33+,34+/m0/s1
SMILES:	CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CCCC[C@@H](CCCCCCCC1=C[C@@H](OC1=O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445024
PubChem CID:	11071966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3409	Goniothalamus leiocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26234	Annona muricata	Species	Annonaceae	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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.353	ug.mL-1	PMID[450705]
NPT4515	Individual Protein	NADH-ubiquinone oxidoreductase chain 1	Bos taurus	IC50	=	1.5	nM	PMID[450706]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.234	ug.mL-1	PMID[450705]

☑ 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 NPC131002 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	168
0.1-0.2	1340
0.2-0.3	5732
0.3-0.4	15092
0.4-0.5	10262
0.5-0.6	6676
0.6-0.7	2691
0.7-0.8	547
0.8-0.85	19
0.85-0.9	26
0.9-0.95	102
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC180363
1.0	High Similarity	NPC65930
1.0	High Similarity	NPC73310
1.0	High Similarity	NPC473712
1.0	High Similarity	NPC473529
1.0	High Similarity	NPC329829
1.0	High Similarity	NPC475159
1.0	High Similarity	NPC94875
1.0	High Similarity	NPC11332
1.0	High Similarity	NPC473780
1.0	High Similarity	NPC145914
0.987	High Similarity	NPC253801
0.987	High Similarity	NPC144415
0.9744	High Similarity	NPC163093
0.9744	High Similarity	NPC156804
0.962	High Similarity	NPC292809
0.962	High Similarity	NPC477014
0.962	High Similarity	NPC319036
0.962	High Similarity	NPC110710
0.962	High Similarity	NPC9678
0.962	High Similarity	NPC39167
0.962	High Similarity	NPC473669
0.962	High Similarity	NPC132496
0.962	High Similarity	NPC66346
0.962	High Similarity	NPC77871
0.962	High Similarity	NPC103284
0.962	High Similarity	NPC100921
0.962	High Similarity	NPC235809
0.962	High Similarity	NPC477013
0.962	High Similarity	NPC231009
0.962	High Similarity	NPC477018
0.962	High Similarity	NPC475268
0.962	High Similarity	NPC286338
0.962	High Similarity	NPC223871
0.962	High Similarity	NPC473156
0.962	High Similarity	NPC473651
0.962	High Similarity	NPC107986
0.962	High Similarity	NPC39279
0.962	High Similarity	NPC473671
0.962	High Similarity	NPC329615
0.962	High Similarity	NPC120398
0.962	High Similarity	NPC82795
0.962	High Similarity	NPC471567
0.962	High Similarity	NPC470400
0.962	High Similarity	NPC473478
0.962	High Similarity	NPC329838
0.962	High Similarity	NPC1083
0.962	High Similarity	NPC283085
0.962	High Similarity	NPC25764
0.962	High Similarity	NPC202055
0.962	High Similarity	NPC322529
0.95	High Similarity	NPC279267
0.95	High Similarity	NPC282815
0.95	High Similarity	NPC134807
0.95	High Similarity	NPC309211
0.95	High Similarity	NPC107717
0.95	High Similarity	NPC62118
0.95	High Similarity	NPC477015
0.95	High Similarity	NPC134865
0.95	High Similarity	NPC171174
0.95	High Similarity	NPC103523
0.95	High Similarity	NPC473840
0.95	High Similarity	NPC293136
0.95	High Similarity	NPC142117
0.95	High Similarity	NPC241360
0.95	High Similarity	NPC475581
0.95	High Similarity	NPC477010
0.95	High Similarity	NPC473687
0.95	High Similarity	NPC210218
0.95	High Similarity	NPC134885
0.95	High Similarity	NPC219652
0.95	High Similarity	NPC69082
0.95	High Similarity	NPC132940
0.95	High Similarity	NPC219498
0.95	High Similarity	NPC232555
0.95	High Similarity	NPC25703
0.95	High Similarity	NPC114694
0.95	High Similarity	NPC231096
0.95	High Similarity	NPC240695
0.95	High Similarity	NPC308412
0.95	High Similarity	NPC204686
0.9383	High Similarity	NPC473649
0.9383	High Similarity	NPC473995
0.9383	High Similarity	NPC159750
0.9383	High Similarity	NPC154097
0.9383	High Similarity	NPC470401
0.9383	High Similarity	NPC476583
0.9383	High Similarity	NPC258068
0.9383	High Similarity	NPC178215
0.9383	High Similarity	NPC477012
0.9383	High Similarity	NPC20533
0.9268	High Similarity	NPC287164
0.9268	High Similarity	NPC100454
0.9268	High Similarity	NPC169511
0.9268	High Similarity	NPC242364
0.9268	High Similarity	NPC261952
0.9268	High Similarity	NPC48338
0.9268	High Similarity	NPC320569
0.9268	High Similarity	NPC280621
0.9268	High Similarity	NPC172821
0.9268	High Similarity	NPC171135
0.9268	High Similarity	NPC234077
0.9268	High Similarity	NPC20339
0.9268	High Similarity	NPC39754
0.9268	High Similarity	NPC133730
0.9268	High Similarity	NPC81045
0.9268	High Similarity	NPC151403
0.9268	High Similarity	NPC191929
0.9268	High Similarity	NPC274446
0.9268	High Similarity	NPC473905
0.9268	High Similarity	NPC89001
0.9268	High Similarity	NPC61257
0.9268	High Similarity	NPC21208
0.9268	High Similarity	NPC320458
0.9268	High Similarity	NPC40376
0.9268	High Similarity	NPC233551
0.9259	High Similarity	NPC112685
0.9157	High Similarity	NPC93794
0.9157	High Similarity	NPC81778
0.9157	High Similarity	NPC42598
0.9157	High Similarity	NPC477011
0.9157	High Similarity	NPC130359
0.9157	High Similarity	NPC14901
0.9157	High Similarity	NPC20621
0.9157	High Similarity	NPC318963
0.9157	High Similarity	NPC477016
0.9157	High Similarity	NPC91067
0.9157	High Similarity	NPC473504
0.9157	High Similarity	NPC139418
0.9157	High Similarity	NPC477017
0.9157	High Similarity	NPC40066
0.9157	High Similarity	NPC280612
0.9136	High Similarity	NPC182383
0.9048	High Similarity	NPC239517
0.9048	High Similarity	NPC473904
0.9024	High Similarity	NPC47937
0.8837	High Similarity	NPC473663
0.8837	High Similarity	NPC475173
0.8837	High Similarity	NPC473561
0.8837	High Similarity	NPC473520
0.8837	High Similarity	NPC473723
0.8837	High Similarity	NPC11456
0.8721	High Similarity	NPC473707
0.8442	Intermediate Similarity	NPC84038
0.8333	Intermediate Similarity	NPC474705
0.8235	Intermediate Similarity	NPC21469
0.8182	Intermediate Similarity	NPC476004
0.8182	Intermediate Similarity	NPC474761
0.8182	Intermediate Similarity	NPC473448
0.809	Intermediate Similarity	NPC30515
0.8072	Intermediate Similarity	NPC47653
0.8068	Intermediate Similarity	NPC295312
0.8052	Intermediate Similarity	NPC218477
0.8	Intermediate Similarity	NPC179746
0.8	Intermediate Similarity	NPC81419
0.8	Intermediate Similarity	NPC273579
0.8	Intermediate Similarity	NPC162205
0.8	Intermediate Similarity	NPC475947
0.8	Intermediate Similarity	NPC288240
0.8	Intermediate Similarity	NPC295204
0.7978	Intermediate Similarity	NPC51004
0.7978	Intermediate Similarity	NPC473619
0.7931	Intermediate Similarity	NPC164393
0.7931	Intermediate Similarity	NPC469483
0.7927	Intermediate Similarity	NPC475711
0.7889	Intermediate Similarity	NPC184463
0.7889	Intermediate Similarity	NPC12172
0.7889	Intermediate Similarity	NPC208886
0.7889	Intermediate Similarity	NPC473321
0.7882	Intermediate Similarity	NPC474291
0.7875	Intermediate Similarity	NPC144419
0.7865	Intermediate Similarity	NPC307411
0.7865	Intermediate Similarity	NPC474032
0.7841	Intermediate Similarity	NPC160138
0.7841	Intermediate Similarity	NPC248602
0.7831	Intermediate Similarity	NPC93763
0.7831	Intermediate Similarity	NPC221095
0.7831	Intermediate Similarity	NPC279214
0.7831	Intermediate Similarity	NPC108816
0.7826	Intermediate Similarity	NPC36954
0.7821	Intermediate Similarity	NPC141481
0.7821	Intermediate Similarity	NPC324981
0.7821	Intermediate Similarity	NPC48218
0.7821	Intermediate Similarity	NPC473559
0.7816	Intermediate Similarity	NPC137033
0.7805	Intermediate Similarity	NPC123360
0.7802	Intermediate Similarity	NPC476300
0.7802	Intermediate Similarity	NPC475912
0.7791	Intermediate Similarity	NPC229799
0.7791	Intermediate Similarity	NPC284472
0.7791	Intermediate Similarity	NPC286770
0.7791	Intermediate Similarity	NPC11620
0.7778	Intermediate Similarity	NPC474098
0.7778	Intermediate Similarity	NPC475995
0.7778	Intermediate Similarity	NPC474321
0.7766	Intermediate Similarity	NPC187268
0.7766	Intermediate Similarity	NPC473326
0.7753	Intermediate Similarity	NPC202672
0.7753	Intermediate Similarity	NPC153805
0.7753	Intermediate Similarity	NPC227379

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 NPC131002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	2097
0.2-0.3	3947
0.3-0.4	2080
0.4-0.5	582
0.5-0.6	240
0.6-0.7	56
0.7-0.8	2
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
0.7778	Intermediate Similarity	NPD6698	Approved
0.7778	Intermediate Similarity	NPD46	Approved
0.74	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7838	Discovery
0.7157	Intermediate Similarity	NPD6686	Approved
0.7128	Intermediate Similarity	NPD7983	Approved
0.7089	Intermediate Similarity	NPD3197	Phase 1
0.6869	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6371	Approved
0.6848	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5785	Approved
0.6813	Remote Similarity	NPD5362	Discontinued
0.6813	Remote Similarity	NPD7154	Phase 3
0.6735	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4756	Discovery
0.6703	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4250	Approved
0.6702	Remote Similarity	NPD4251	Approved
0.67	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4249	Approved
0.6535	Remote Similarity	NPD7638	Approved
0.65	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD8039	Approved
0.6471	Remote Similarity	NPD7639	Approved
0.6471	Remote Similarity	NPD7640	Approved
0.6444	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5344	Discontinued
0.6392	Remote Similarity	NPD1695	Approved
0.6386	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3196	Approved
0.6364	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD4266	Approved
0.6364	Remote Similarity	NPD3730	Approved
0.6364	Remote Similarity	NPD3728	Approved
0.6364	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD3194	Approved
0.6364	Remote Similarity	NPD3195	Phase 2
0.6344	Remote Similarity	NPD6435	Approved
0.6344	Remote Similarity	NPD4269	Approved
0.6344	Remote Similarity	NPD5209	Approved
0.6344	Remote Similarity	NPD4270	Approved
0.6337	Remote Similarity	NPD7839	Suspended
0.6316	Remote Similarity	NPD1694	Approved
0.6304	Remote Similarity	NPD4252	Approved
0.6296	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6110	Phase 1
0.6277	Remote Similarity	NPD5332	Approved
0.6277	Remote Similarity	NPD5331	Approved
0.6273	Remote Similarity	NPD6053	Discontinued
0.6264	Remote Similarity	NPD4271	Approved
0.6264	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD6109	Phase 1
0.625	Remote Similarity	NPD5786	Approved
0.6237	Remote Similarity	NPD5369	Approved
0.6237	Remote Similarity	NPD4790	Discontinued
0.6234	Remote Similarity	NPD3172	Approved
0.6195	Remote Similarity	NPD7115	Discovery
0.6186	Remote Similarity	NPD7507	Approved
0.6184	Remote Similarity	NPD6927	Phase 3
0.6145	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4820	Approved
0.6129	Remote Similarity	NPD4819	Approved
0.6129	Remote Similarity	NPD4821	Approved
0.6129	Remote Similarity	NPD5368	Approved
0.6129	Remote Similarity	NPD4822	Approved
0.6121	Remote Similarity	NPD8516	Approved
0.6121	Remote Similarity	NPD8517	Approved
0.6121	Remote Similarity	NPD8515	Approved
0.6121	Remote Similarity	NPD8513	Phase 3
0.6118	Remote Similarity	NPD3704	Approved
0.6033	Remote Similarity	NPD7319	Approved
0.6017	Remote Similarity	NPD7829	Approved
0.6017	Remote Similarity	NPD7830	Approved
0.6	Remote Similarity	NPD6648	Approved
0.598	Remote Similarity	NPD7748	Approved
0.598	Remote Similarity	NPD5282	Discontinued
0.5974	Remote Similarity	NPD28	Approved
0.5974	Remote Similarity	NPD29	Approved
0.5963	Remote Similarity	NPD6412	Phase 2
0.5946	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7637	Suspended
0.593	Remote Similarity	NPD7331	Phase 2
0.593	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6101	Approved
0.59	Remote Similarity	NPD5370	Suspended
0.5897	Remote Similarity	NPD8294	Approved
0.5897	Remote Similarity	NPD8377	Approved
0.5893	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7632	Discontinued
0.5868	Remote Similarity	NPD8074	Phase 3
0.5865	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7327	Approved
0.5862	Remote Similarity	NPD7328	Approved
0.5854	Remote Similarity	NPD9119	Approved
0.5854	Remote Similarity	NPD69	Approved
0.5847	Remote Similarity	NPD8335	Approved
0.5847	Remote Similarity	NPD8378	Approved
0.5847	Remote Similarity	NPD8033	Approved
0.5847	Remote Similarity	NPD8380	Approved
0.5847	Remote Similarity	NPD8379	Approved
0.5847	Remote Similarity	NPD8296	Approved
0.5841	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD6647	Phase 2
0.5827	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7516	Approved
0.581	Remote Similarity	NPD6083	Phase 2
0.581	Remote Similarity	NPD6084	Phase 2
0.581	Remote Similarity	NPD7902	Approved
0.58	Remote Similarity	NPD6903	Approved
0.5789	Remote Similarity	NPD4632	Approved
0.5784	Remote Similarity	NPD7515	Phase 2
0.5784	Remote Similarity	NPD6411	Approved
0.5784	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7521	Approved
0.5758	Remote Similarity	NPD5330	Approved
0.5758	Remote Similarity	NPD6422	Discontinued
0.5758	Remote Similarity	NPD7334	Approved
0.5758	Remote Similarity	NPD7146	Approved
0.5758	Remote Similarity	NPD6409	Approved
0.5758	Remote Similarity	NPD6684	Approved
0.575	Remote Similarity	NPD7642	Approved
0.5732	Remote Similarity	NPD9118	Approved
0.5728	Remote Similarity	NPD6399	Phase 3
0.5726	Remote Similarity	NPD7641	Discontinued
0.5714	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD3173	Approved
0.5702	Remote Similarity	NPD7492	Approved
0.5698	Remote Similarity	NPD7909	Approved
0.5691	Remote Similarity	NPD7736	Approved
0.5688	Remote Similarity	NPD2259	Approved
0.5688	Remote Similarity	NPD2258	Approved
0.5676	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6421	Discontinued
0.5664	Remote Similarity	NPD2067	Discontinued
0.5656	Remote Similarity	NPD8273	Phase 1
0.5656	Remote Similarity	NPD6616	Approved
0.5652	Remote Similarity	NPD8133	Approved
0.5644	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6672	Approved
0.5644	Remote Similarity	NPD5737	Approved
0.5641	Remote Similarity	NPD7505	Discontinued
0.5641	Remote Similarity	NPD7500	Approved
0.563	Remote Similarity	NPD6319	Approved
0.563	Remote Similarity	NPD6054	Approved
0.5625	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7320	Approved
0.5625	Remote Similarity	NPD6881	Approved
0.5625	Remote Similarity	NPD6899	Approved
0.5619	Remote Similarity	NPD5695	Phase 3
0.5614	Remote Similarity	NPD8130	Phase 1
0.5614	Remote Similarity	NPD2204	Approved
0.561	Remote Similarity	NPD8293	Discontinued
0.561	Remote Similarity	NPD7078	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