NPASS Compound

Structure

CID90822 OpenBabel06191715432D 52 61 0 0 1 0 0 0 0 0999 V2000 3.0574 0.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4763 0.1351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8295 -4.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7287 -4.9331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7529 -1.3533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7529 0.2851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5304 1.7735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9493 0.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1219 -5.3265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4364 -5.8328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6988 -1.3533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6988 0.2851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6278 -3.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5685 -0.7102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2663 -3.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0650 -0.0172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3286 -2.1084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5304 0.1351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0957 -4.2302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2799 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4763 1.7735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4889 -6.0295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1718 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4470 -4.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4836 -0.2424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6278 -3.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2557 -1.0682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2438 -1.6407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2663 -3.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6278 -0.2040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0159 -2.4664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4470 -2.5275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6278 -0.8642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6437 -1.6022 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.7965 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3880 -2.2624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3880 -1.6022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0682 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8251 -1.4154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5845 -1.5034 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3880 -3.3305 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3880 -0.5341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9493 2.5927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7812 -6.9291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1177 -0.5341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4470 -6.3112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2489 0.3136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0090 -1.0847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8676 -0.4704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9692 -2.3675 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 -1.0159 -3.1265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 18 2 0 0 0 0 2 8 2 0 0 0 0 2 18 1 0 0 0 0 3 9 1 0 0 0 0 3 19 2 0 0 0 0 4 10 2 0 0 0 0 4 19 1 0 0 0 0 5 11 1 0 0 0 0 5 20 2 0 0 0 0 6 12 2 0 0 0 0 6 20 1 0 0 0 0 7 21 2 0 0 0 0 8 21 1 0 0 0 0 9 22 2 0 0 0 0 10 22 1 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 13 26 1 0 0 0 0 14 25 2 0 0 0 0 14 27 1 0 0 0 0 15 24 1 0 0 0 0 15 29 2 0 0 0 0 16 25 1 0 0 0 0 16 30 2 0 0 0 0 17 28 1 0 0 0 0 17 31 2 0 0 0 0 21 43 1 0 0 0 0 22 44 1 0 0 0 0 23 45 1 0 0 0 0 24 46 1 0 0 0 0 25 47 1 0 0 0 0 26 32 2 0 0 0 0 27 33 2 0 0 0 0 28 39 1 0 0 0 0 28 48 2 0 0 0 0 29 32 1 0 0 0 0 29 50 1 0 0 0 0 30 33 1 0 0 0 0 30 51 1 0 0 0 0 31 36 1 0 0 0 0 31 52 1 0 0 0 0 32 34 1 0 0 0 0 34 27 1 1 0 0 0 34 40 1 0 0 0 0 35 26 1 1 0 0 0 35 36 1 0 0 0 0 35 41 1 0 0 0 0 36 37 2 0 0 0 0 37 38 1 0 0 0 0 37 39 1 0 0 0 0 38 33 1 6 0 0 0 38 42 1 0 0 0 0 39 49 2 0 0 0 0 40 18 1 6 0 0 0 40 50 1 0 0 0 0 41 19 1 6 0 0 0 41 52 1 0 0 0 0 42 20 1 1 0 0 0 42 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	692.17
Volume:	687.233
LogP:	7.0
LogD:	3.808
LogS:	-3.897
# Rotatable Bonds:	3
TPSA:	173.21
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	10
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	5.062
Fsp3:	0.095
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.032
MDCK Permeability:	7.537541023339145e-06
Pgp-inhibitor:	0.162
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.809
20% Bioavailability (F20%):	0.712
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	97.72379302978516%
Volume Distribution (VD):	0.462
Pgp-substrate:	2.804764986038208%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.441
CYP2C19-inhibitor:	0.949
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.743
CYP2C9-substrate:	0.993
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.813
CYP3A4-inhibitor:	0.193
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	7.392
Half-life (T1/2):	0.224

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.364
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.571
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.81
Skin Sensitization:	0.803
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.892
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC90822

Natural Product ID:	NPC90822
*Common Name:**	Hopeanolin
IUPAC Name:	n.a.
Synonyms:	Hopeanolin
Standard InCHIKey:	PEVCENMPFGEBKL-MGZRWOOSSA-N
Standard InCHI:	InChI=1S/C42H28O10/c43-21-7-1-18(2-8-21)40-34-27-14-25(47)16-30-33(27)38(42(51-30)20-5-11-23(45)12-6-20)37-36-31(17-28(48)39(37)49)52-41(19-3-9-22(44)10-4-19)35(36)26-13-24(46)15-29(50-40)32(26)34/h1-17,34-35,38,40-47H/t34-,35-,38-,40+,41+,42-/m1/s1
SMILES:	Oc1ccc(cc1)[C@@H]1OC2=CC(=O)C(=O)C3=C2[C@H]1c1cc(O)cc2c1[C@H]([C@@H](O2)c1ccc(cc1)O)c1c2[C@H]3[C@H](Oc2cc(c1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502987
PubChem CID:	16099540
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO14000	Hopea exalata	Species	Dipterocarpaceae	Eukaryota	stem bark	Botanical Garden at Jianfeng Town, Ledong County, Hainan Province, China	2004-JUL	PMID[17190464]
NPO2042	Garcinia bancana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2042	Garcinia bancana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16805	Senecio cisplatinus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16691	Viguiera radula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13778	Melandrium turkestanicum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14476	Sterculia alata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2042	Garcinia bancana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14958	Duguetia eximia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17995	Xeromphis spinosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14000	Hopea exalata	Species	Dipterocarpaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	MIC	=	0.1	ug.mL-1	PMID[506680]
NPT1199	Organism	Valsa mali	Valsa mali	MIC	=	1.55	ug.mL-1	PMID[506680]
NPT2705	Organism	Alternaria solani	Alternaria solani	MIC	=	1.56	ug.mL-1	PMID[506680]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	MIC	=	6.22	ug.mL-1	PMID[506680]
NPT2637	Organism	Colletotrichum lagenarium	Colletotrichum lagenarium	MIC	=	10.6	ug.mL-1	PMID[506680]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	=	22.5	ug.mL-1	PMID[506680]

☑ 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 NPC90822 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	419
0.1-0.2	1614
0.2-0.3	3115
0.3-0.4	8093
0.4-0.5	11076
0.5-0.6	4041
0.6-0.7	7053
0.7-0.8	6981
0.8-0.85	265
0.85-0.9	39
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8954	High Similarity	NPC176804
0.8954	High Similarity	NPC71686
0.8889	High Similarity	NPC149633
0.8827	High Similarity	NPC261896
0.8802	High Similarity	NPC300657
0.8774	High Similarity	NPC6702
0.8774	High Similarity	NPC133209
0.8774	High Similarity	NPC112819
0.8718	High Similarity	NPC77903
0.8718	High Similarity	NPC17101
0.865	High Similarity	NPC301256
0.865	High Similarity	NPC312273
0.8598	High Similarity	NPC473012
0.8545	High Similarity	NPC473009
0.8535	High Similarity	NPC224921
0.8535	High Similarity	NPC237546
0.8535	High Similarity	NPC231712
0.8535	High Similarity	NPC242774
0.8535	High Similarity	NPC111134
0.8528	High Similarity	NPC195167
0.8519	High Similarity	NPC55463
0.8519	High Similarity	NPC166116
0.8494	Intermediate Similarity	NPC474591
0.8494	Intermediate Similarity	NPC473010
0.8491	Intermediate Similarity	NPC218801
0.8485	Intermediate Similarity	NPC473011
0.8476	Intermediate Similarity	NPC184326
0.8476	Intermediate Similarity	NPC292863
0.8466	Intermediate Similarity	NPC287789
0.8466	Intermediate Similarity	NPC271741
0.8457	Intermediate Similarity	NPC201227
0.8457	Intermediate Similarity	NPC258474
0.8438	Intermediate Similarity	NPC105073
0.8438	Intermediate Similarity	NPC224528
0.8438	Intermediate Similarity	NPC157081
0.8438	Intermediate Similarity	NPC233886
0.8434	Intermediate Similarity	NPC214279
0.8428	Intermediate Similarity	NPC106328
0.8428	Intermediate Similarity	NPC35150
0.8424	Intermediate Similarity	NPC18380
0.8424	Intermediate Similarity	NPC137232
0.8421	Intermediate Similarity	NPC11727
0.8421	Intermediate Similarity	NPC15109
0.8415	Intermediate Similarity	NPC55443
0.8415	Intermediate Similarity	NPC105584
0.8415	Intermediate Similarity	NPC18699
0.8405	Intermediate Similarity	NPC61112
0.8405	Intermediate Similarity	NPC32867
0.8405	Intermediate Similarity	NPC309648
0.8405	Intermediate Similarity	NPC198489
0.8405	Intermediate Similarity	NPC69531
0.8395	Intermediate Similarity	NPC121568
0.8383	Intermediate Similarity	NPC169471
0.8364	Intermediate Similarity	NPC226462
0.8364	Intermediate Similarity	NPC98023
0.8364	Intermediate Similarity	NPC195136
0.8364	Intermediate Similarity	NPC42965
0.8354	Intermediate Similarity	NPC257166
0.8354	Intermediate Similarity	NPC14468
0.8354	Intermediate Similarity	NPC1796
0.8344	Intermediate Similarity	NPC202104
0.8344	Intermediate Similarity	NPC254351
0.8333	Intermediate Similarity	NPC39154
0.8333	Intermediate Similarity	NPC174086
0.8333	Intermediate Similarity	NPC78324
0.8333	Intermediate Similarity	NPC82330
0.8333	Intermediate Similarity	NPC115601
0.8333	Intermediate Similarity	NPC251336
0.8333	Intermediate Similarity	NPC208011
0.8323	Intermediate Similarity	NPC290160
0.8313	Intermediate Similarity	NPC107862
0.8313	Intermediate Similarity	NPC180605
0.8313	Intermediate Similarity	NPC122980
0.8313	Intermediate Similarity	NPC148516
0.8313	Intermediate Similarity	NPC177172
0.8303	Intermediate Similarity	NPC15815
0.8303	Intermediate Similarity	NPC51247
0.8303	Intermediate Similarity	NPC295090
0.8284	Intermediate Similarity	NPC286230
0.8284	Intermediate Similarity	NPC253730
0.8274	Intermediate Similarity	NPC469664
0.8272	Intermediate Similarity	NPC120633
0.8272	Intermediate Similarity	NPC473018
0.8266	Intermediate Similarity	NPC478000
0.8263	Intermediate Similarity	NPC477239
0.8263	Intermediate Similarity	NPC3448
0.8263	Intermediate Similarity	NPC15374
0.8242	Intermediate Similarity	NPC318527
0.8242	Intermediate Similarity	NPC475184
0.8242	Intermediate Similarity	NPC323627
0.8242	Intermediate Similarity	NPC322459
0.8242	Intermediate Similarity	NPC324358
0.8242	Intermediate Similarity	NPC208258
0.8232	Intermediate Similarity	NPC79375
0.8232	Intermediate Similarity	NPC37253
0.8232	Intermediate Similarity	NPC300668
0.8232	Intermediate Similarity	NPC66441
0.8232	Intermediate Similarity	NPC182555
0.8232	Intermediate Similarity	NPC134171
0.8225	Intermediate Similarity	NPC171985
0.8225	Intermediate Similarity	NPC224851
0.8225	Intermediate Similarity	NPC320741
0.8214	Intermediate Similarity	NPC38591
0.8205	Intermediate Similarity	NPC182509
0.8205	Intermediate Similarity	NPC213607
0.8205	Intermediate Similarity	NPC174787
0.8204	Intermediate Similarity	NPC273467
0.8204	Intermediate Similarity	NPC189552
0.8199	Intermediate Similarity	NPC122894
0.8187	Intermediate Similarity	NPC91043
0.8182	Intermediate Similarity	NPC137100
0.8182	Intermediate Similarity	NPC125579
0.8182	Intermediate Similarity	NPC54830
0.8182	Intermediate Similarity	NPC56049
0.8171	Intermediate Similarity	NPC157333
0.8161	Intermediate Similarity	NPC475783
0.816	Intermediate Similarity	NPC178484
0.8155	Intermediate Similarity	NPC149389
0.8148	Intermediate Similarity	NPC288840
0.8148	Intermediate Similarity	NPC291746
0.8148	Intermediate Similarity	NPC3642
0.8148	Intermediate Similarity	NPC132345
0.8144	Intermediate Similarity	NPC472052
0.8144	Intermediate Similarity	NPC121647
0.8144	Intermediate Similarity	NPC312993
0.8144	Intermediate Similarity	NPC470342
0.8144	Intermediate Similarity	NPC472060
0.8144	Intermediate Similarity	NPC186325
0.814	Intermediate Similarity	NPC478002
0.814	Intermediate Similarity	NPC477529
0.8137	Intermediate Similarity	NPC142863
0.8129	Intermediate Similarity	NPC300307
0.8129	Intermediate Similarity	NPC141717
0.8129	Intermediate Similarity	NPC107627
0.8125	Intermediate Similarity	NPC212697
0.8125	Intermediate Similarity	NPC471473
0.8125	Intermediate Similarity	NPC471524
0.8125	Intermediate Similarity	NPC150977
0.8125	Intermediate Similarity	NPC471523
0.8121	Intermediate Similarity	NPC215203
0.8121	Intermediate Similarity	NPC265624
0.8121	Intermediate Similarity	NPC159707
0.8121	Intermediate Similarity	NPC186227
0.8121	Intermediate Similarity	NPC150908
0.8121	Intermediate Similarity	NPC121649
0.8121	Intermediate Similarity	NPC248739
0.8121	Intermediate Similarity	NPC205026
0.8121	Intermediate Similarity	NPC14606
0.8121	Intermediate Similarity	NPC100049
0.8121	Intermediate Similarity	NPC158027
0.8121	Intermediate Similarity	NPC52611
0.8118	Intermediate Similarity	NPC477835
0.8113	Intermediate Similarity	NPC15659
0.8113	Intermediate Similarity	NPC304894
0.811	Intermediate Similarity	NPC474843
0.811	Intermediate Similarity	NPC43345
0.811	Intermediate Similarity	NPC207624
0.8107	Intermediate Similarity	NPC63438
0.8107	Intermediate Similarity	NPC159508
0.8095	Intermediate Similarity	NPC139540
0.8095	Intermediate Similarity	NPC231758
0.8095	Intermediate Similarity	NPC472261
0.8095	Intermediate Similarity	NPC177100
0.8092	Intermediate Similarity	NPC59491
0.8092	Intermediate Similarity	NPC24748
0.8092	Intermediate Similarity	NPC98583
0.809	Intermediate Similarity	NPC73929
0.809	Intermediate Similarity	NPC139683
0.809	Intermediate Similarity	NPC47905
0.8084	Intermediate Similarity	NPC177650
0.8084	Intermediate Similarity	NPC51760
0.8084	Intermediate Similarity	NPC226287
0.8084	Intermediate Similarity	NPC40583
0.8081	Intermediate Similarity	NPC180768
0.807	Intermediate Similarity	NPC215802
0.807	Intermediate Similarity	NPC167231
0.8061	Intermediate Similarity	NPC71061
0.8061	Intermediate Similarity	NPC72425
0.8061	Intermediate Similarity	NPC194593
0.8061	Intermediate Similarity	NPC303485
0.8061	Intermediate Similarity	NPC324447
0.8061	Intermediate Similarity	NPC290830
0.8059	Intermediate Similarity	NPC477840
0.805	Intermediate Similarity	NPC173203
0.805	Intermediate Similarity	NPC163508
0.8049	Intermediate Similarity	NPC317715
0.8049	Intermediate Similarity	NPC476391
0.8049	Intermediate Similarity	NPC138299
0.8049	Intermediate Similarity	NPC222713
0.8049	Intermediate Similarity	NPC476551
0.8049	Intermediate Similarity	NPC316960
0.8049	Intermediate Similarity	NPC111112
0.8049	Intermediate Similarity	NPC23668
0.8049	Intermediate Similarity	NPC58668
0.8049	Intermediate Similarity	NPC148945
0.8049	Intermediate Similarity	NPC115324
0.8049	Intermediate Similarity	NPC476553
0.8049	Intermediate Similarity	NPC78835
0.8049	Intermediate Similarity	NPC204561
0.8049	Intermediate Similarity	NPC106372

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 NPC90822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	920
0.2-0.3	1549
0.3-0.4	2667
0.4-0.5	2032
0.5-0.6	1075
0.6-0.7	422
0.7-0.8	116
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8204	Intermediate Similarity	NPD6959	Discontinued
0.8121	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD3750	Approved
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7819	Suspended
0.7829	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7199	Phase 2
0.775	Intermediate Similarity	NPD1549	Phase 2
0.7746	Intermediate Similarity	NPD6166	Phase 2
0.7746	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4908	Phase 1
0.7688	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6234	Discontinued
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD7768	Phase 2
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.7647	Intermediate Similarity	NPD4965	Approved
0.7633	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7229	Phase 3
0.7628	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6099	Approved
0.7625	Intermediate Similarity	NPD6100	Approved
0.7619	Intermediate Similarity	NPD7411	Suspended
0.7576	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1934	Approved
0.7562	Intermediate Similarity	NPD3748	Approved
0.7562	Intermediate Similarity	NPD1510	Phase 2
0.756	Intermediate Similarity	NPD4380	Phase 2
0.7557	Intermediate Similarity	NPD7228	Approved
0.7557	Intermediate Similarity	NPD3818	Discontinued
0.7544	Intermediate Similarity	NPD3882	Suspended
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2796	Approved
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.7514	Intermediate Similarity	NPD5494	Approved
0.7514	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD8313	Approved
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD37	Approved
0.7458	Intermediate Similarity	NPD3751	Discontinued
0.7429	Intermediate Similarity	NPD3787	Discontinued
0.7429	Intermediate Similarity	NPD6232	Discontinued
0.7427	Intermediate Similarity	NPD2801	Approved
0.7423	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1511	Approved
0.7399	Intermediate Similarity	NPD7075	Discontinued
0.7386	Intermediate Similarity	NPD1610	Phase 2
0.7378	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7074	Phase 3
0.7365	Intermediate Similarity	NPD2533	Approved
0.7365	Intermediate Similarity	NPD2534	Approved
0.7365	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD1465	Phase 2
0.7322	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1512	Approved
0.7318	Intermediate Similarity	NPD7054	Approved
0.7318	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1240	Approved
0.7297	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7472	Approved
0.7273	Intermediate Similarity	NPD2800	Approved
0.7253	Intermediate Similarity	NPD7808	Phase 3
0.7238	Intermediate Similarity	NPD6797	Phase 2
0.7225	Intermediate Similarity	NPD8455	Phase 2
0.7225	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1607	Approved
0.7215	Intermediate Similarity	NPD2861	Phase 2
0.7202	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7240	Approved
0.7198	Intermediate Similarity	NPD6559	Discontinued
0.7198	Intermediate Similarity	NPD7251	Discontinued
0.7188	Intermediate Similarity	NPD3764	Approved
0.7188	Intermediate Similarity	NPD3268	Approved
0.7184	Intermediate Similarity	NPD5402	Approved
0.7184	Intermediate Similarity	NPD3817	Phase 2
0.7176	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6801	Discontinued
0.7158	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2344	Approved
0.7128	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7003	Approved
0.7125	Intermediate Similarity	NPD4625	Phase 3
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7118	Intermediate Similarity	NPD6273	Approved
0.7113	Intermediate Similarity	NPD7680	Approved
0.7101	Intermediate Similarity	NPD6799	Approved
0.7099	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1613	Approved
0.7095	Intermediate Similarity	NPD3926	Phase 2
0.7093	Intermediate Similarity	NPD3226	Approved
0.7089	Intermediate Similarity	NPD2797	Approved
0.7076	Intermediate Similarity	NPD5403	Approved
0.707	Intermediate Similarity	NPD4749	Approved
0.7065	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6599	Discontinued
0.703	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7033	Discontinued
0.7024	Intermediate Similarity	NPD4628	Phase 3
0.7024	Intermediate Similarity	NPD8166	Discontinued
0.7021	Intermediate Similarity	NPD4287	Approved
0.7011	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1608	Approved
0.6994	Remote Similarity	NPD7458	Discontinued
0.6989	Remote Similarity	NPD4288	Approved
0.6988	Remote Similarity	NPD1551	Phase 2
0.6983	Remote Similarity	NPD8127	Discontinued
0.6982	Remote Similarity	NPD2309	Approved
0.6978	Remote Similarity	NPD7177	Discontinued
0.6975	Remote Similarity	NPD6798	Discontinued
0.6975	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5401	Approved
0.6957	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6355	Discontinued
0.6951	Remote Similarity	NPD5124	Phase 1
0.6951	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8151	Discontinued
0.6918	Remote Similarity	NPD3225	Approved
0.6915	Remote Similarity	NPD8434	Phase 2
0.6909	Remote Similarity	NPD6651	Approved
0.6904	Remote Similarity	NPD7871	Phase 2
0.6904	Remote Similarity	NPD7870	Phase 2
0.6901	Remote Similarity	NPD7213	Phase 3
0.6901	Remote Similarity	NPD7212	Phase 2
0.6894	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4060	Phase 1
0.6886	Remote Similarity	NPD5405	Approved
0.6886	Remote Similarity	NPD5404	Approved
0.6886	Remote Similarity	NPD5406	Approved
0.6886	Remote Similarity	NPD5408	Approved
0.6882	Remote Similarity	NPD6190	Approved
0.6879	Remote Similarity	NPD920	Approved
0.6875	Remote Similarity	NPD3266	Approved
0.6875	Remote Similarity	NPD3267	Approved
0.6865	Remote Similarity	NPD5953	Discontinued
0.686	Remote Similarity	NPD7447	Phase 1
0.686	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5711	Approved
0.6851	Remote Similarity	NPD5710	Approved
0.6845	Remote Similarity	NPD6005	Phase 3
0.6845	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6002	Phase 3
0.6845	Remote Similarity	NPD6004	Phase 3
0.6845	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD5761	Phase 2
0.6836	Remote Similarity	NPD5760	Phase 2
0.6835	Remote Similarity	NPD422	Phase 1
0.6829	Remote Similarity	NPD8032	Phase 2
0.6828	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2799	Discontinued
0.6825	Remote Similarity	NPD8150	Discontinued
0.6824	Remote Similarity	NPD3892	Phase 2
0.6821	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6971	Discontinued
0.6815	Remote Similarity	NPD17	Approved
0.6813	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3027	Phase 3
0.6809	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7037	Approved
0.6788	Remote Similarity	NPD943	Approved
0.6786	Remote Similarity	NPD6779	Approved
0.6786	Remote Similarity	NPD6780	Approved
0.6786	Remote Similarity	NPD6777	Approved
0.6786	Remote Similarity	NPD6781	Approved
0.6786	Remote Similarity	NPD6782	Approved
0.6786	Remote Similarity	NPD2935	Discontinued
0.6786	Remote Similarity	NPD6778	Approved
0.6786	Remote Similarity	NPD6776	Approved
0.6768	Remote Similarity	NPD7698	Approved
0.6768	Remote Similarity	NPD7696	Phase 3
0.6768	Remote Similarity	NPD7697	Approved
0.6766	Remote Similarity	NPD7097	Phase 1
0.6765	Remote Similarity	NPD1243	Approved
0.6763	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2346	Discontinued
0.6728	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6233	Phase 2
0.6726	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7466	Approved
0.6718	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1247	Approved
0.6701	Remote Similarity	NPD4360	Phase 2
0.6701	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4363	Phase 3
0.67	Remote Similarity	NPD7783	Phase 2
0.67	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4140	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