NPASS Compound

Structure

CID59491 OpenBabel06191715392D 42 49 0 0 1 0 0 0 0 0999 V2000 -0.8537 4.3169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7841 -0.3046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2637 -1.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1547 1.4213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2716 -1.2963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3312 1.9027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7819 -0.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6745 2.8793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0206 2.8854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4758 1.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1829 0.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6520 0.0221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8424 -2.1444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8248 -1.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3210 -0.0050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8499 3.3593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8248 -0.3046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4758 0.4978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8018 -2.1329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7841 -1.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1496 0.4675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5026 1.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6752 1.9152 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0061 1.9258 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8225 -0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3528 -1.3193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6520 1.9247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3066 0.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3452 -1.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4975 0.4763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8281 0.4978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8281 1.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 1.4413 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8342 0.4767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2915 -2.9580 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2637 -2.7969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9778 -0.0166 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6066 -1.3308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6520 2.8840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4069 -0.9359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6682 0.0024 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 16 1 0 0 0 0 2 3 2 0 0 0 0 2 17 1 0 0 0 0 3 20 1 0 0 0 0 4 6 2 0 0 0 0 4 21 1 0 0 0 0 5 7 2 0 0 0 0 5 19 1 0 0 0 0 6 22 1 0 0 0 0 7 25 1 0 0 0 0 8 16 1 0 0 0 0 9 16 2 0 0 0 0 10 18 2 0 0 0 0 10 27 1 0 0 0 0 11 17 1 0 0 0 0 11 28 2 0 0 0 0 12 18 1 0 0 0 0 12 31 2 0 0 0 0 13 19 2 0 0 0 0 13 26 1 0 0 0 0 14 20 2 0 0 0 0 14 29 1 0 0 0 0 15 21 2 0 0 0 0 15 30 1 0 0 0 0 17 29 2 0 0 0 0 18 28 1 0 0 0 0 19 35 1 0 0 0 0 20 36 1 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 30 2 0 0 0 0 23 8 1 1 0 0 0 23 33 1 0 0 0 0 24 9 1 6 0 0 0 24 32 1 0 0 0 0 24 33 1 0 0 0 0 25 26 2 0 0 0 0 26 38 1 0 0 0 0 27 32 2 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 40 1 0 0 0 0 30 41 1 0 0 0 0 31 32 1 0 0 0 0 31 42 1 0 0 0 0 33 34 1 0 0 0 0 34 25 1 1 0 0 0 34 41 1 0 0 0 0 34 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.16
Volume:	561.58
LogP:	6.533
LogD:	3.714
LogS:	-2.748
# Rotatable Bonds:	2
TPSA:	132.75
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.144
Synthetic Accessibility Score:	4.542
Fsp3:	0.176
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:	-5.335
MDCK Permeability:	1.03183865576284e-05
Pgp-inhibitor:	0.121
Pgp-substrate:	0.372
Human Intestinal Absorption (HIA):	0.577
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	94.58140563964844%
Volume Distribution (VD):	0.696
Pgp-substrate:	2.5469918251037598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.541
CYP1A2-substrate:	0.376
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.906
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.791
CYP2D6-substrate:	0.658
CYP3A4-inhibitor:	0.779
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	7.516
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.492
Rat Oral Acute Toxicity:	0.85
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.948
Carcinogencity:	0.893
Eye Corrosion:	0.003
Eye Irritation:	0.879
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC59491

Natural Product ID:	NPC59491
*Common Name:**	Albanol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MJJWBJFYYRAYKU-WLKQUGLZSA-N
Standard InCHI:	InChI=1S/C34H26O8/c1-16-8-23-22-6-4-21(37)15-30(22)41-34(25-7-5-19(35)13-26(25)38)33(23)24(9-16)32-27(39)10-18(12-31(32)42-34)28-11-17-2-3-20(36)14-29(17)40-28/h2-7,9-15,23-24,33,35-39H,8H2,1H3/t23-,24-,33?,34+/m1/s1
SMILES:	CC1=C[C@@H]2c3c(cc(cc3O[C@@]3(c4ccc(cc4O)O)C2[C@H](C1)c1ccc(cc1O3)O)c1cc2ccc(cc2o1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454705
PubChem CID:	44567218
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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5495	Broussonetia papyrifera	Species	Moraceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	7500.0	nM	PMID[552599]

☑ 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 NPC59491 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	438
0.1-0.2	1717
0.2-0.3	3704
0.3-0.4	9526
0.4-0.5	9338
0.5-0.6	3794
0.6-0.7	5955
0.7-0.8	5501
0.8-0.85	2485
0.85-0.9	223
0.9-0.95	6
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC24748
0.9877	High Similarity	NPC101991
0.9758	High Similarity	NPC121888
0.9627	High Similarity	NPC169471
0.9509	High Similarity	NPC286230
0.9509	High Similarity	NPC253730
0.9444	High Similarity	NPC159508
0.9193	High Similarity	NPC137100
0.9	High Similarity	NPC300657
0.897	High Similarity	NPC312273
0.897	High Similarity	NPC301256
0.8941	High Similarity	NPC73899
0.8941	High Similarity	NPC474276
0.8941	High Similarity	NPC17105
0.8941	High Similarity	NPC147363
0.8922	High Similarity	NPC473010
0.8916	High Similarity	NPC473012
0.8882	High Similarity	NPC167576
0.8869	High Similarity	NPC251336
0.8862	High Similarity	NPC473009
0.8862	High Similarity	NPC38591
0.8848	High Similarity	NPC51760
0.8848	High Similarity	NPC105584
0.8841	High Similarity	NPC56049
0.8841	High Similarity	NPC54830
0.8834	High Similarity	NPC72370
0.8817	High Similarity	NPC292233
0.8802	High Similarity	NPC15374
0.8795	High Similarity	NPC312993
0.8795	High Similarity	NPC195136
0.8788	High Similarity	NPC271741
0.8788	High Similarity	NPC96342
0.8788	High Similarity	NPC212967
0.8788	High Similarity	NPC287789
0.8788	High Similarity	NPC246647
0.8788	High Similarity	NPC164110
0.8765	High Similarity	NPC470206
0.8765	High Similarity	NPC78335
0.8765	High Similarity	NPC470207
0.8765	High Similarity	NPC230713
0.875	High Similarity	NPC87583
0.8743	High Similarity	NPC189552
0.8743	High Similarity	NPC273467
0.8736	High Similarity	NPC114257
0.8736	High Similarity	NPC299149
0.8736	High Similarity	NPC153578
0.8736	High Similarity	NPC277710
0.8735	High Similarity	NPC472877
0.8735	High Similarity	NPC177650
0.8727	High Similarity	NPC69531
0.8727	High Similarity	NPC61112
0.8727	High Similarity	NPC198489
0.8727	High Similarity	NPC180924
0.8727	High Similarity	NPC309648
0.872	High Similarity	NPC472462
0.872	High Similarity	NPC235333
0.872	High Similarity	NPC213608
0.872	High Similarity	NPC1477
0.8713	High Similarity	NPC477572
0.8713	High Similarity	NPC287884
0.8713	High Similarity	NPC477571
0.8713	High Similarity	NPC477573
0.8713	High Similarity	NPC8704
0.8712	High Similarity	NPC149085
0.8712	High Similarity	NPC170169
0.8712	High Similarity	NPC193976
0.8712	High Similarity	NPC23668
0.8704	High Similarity	NPC178202
0.8698	High Similarity	NPC474591
0.869	High Similarity	NPC477239
0.869	High Similarity	NPC477528
0.869	High Similarity	NPC3448
0.869	High Similarity	NPC473011
0.8683	High Similarity	NPC186325
0.8683	High Similarity	NPC472052
0.8683	High Similarity	NPC98023
0.8683	High Similarity	NPC470342
0.8683	High Similarity	NPC226462
0.8683	High Similarity	NPC472060
0.8678	High Similarity	NPC478000
0.8675	High Similarity	NPC268360
0.8675	High Similarity	NPC1796
0.8675	High Similarity	NPC65504
0.8675	High Similarity	NPC475184
0.8667	High Similarity	NPC14606
0.8667	High Similarity	NPC300668
0.8667	High Similarity	NPC100049
0.8667	High Similarity	NPC158027
0.8667	High Similarity	NPC215203
0.8667	High Similarity	NPC297531
0.8667	High Similarity	NPC265624
0.8667	High Similarity	NPC148938
0.8667	High Similarity	NPC159707
0.8667	High Similarity	NPC213936
0.8667	High Similarity	NPC258474
0.8667	High Similarity	NPC201227
0.8667	High Similarity	NPC248739
0.8667	High Similarity	NPC134171
0.8667	High Similarity	NPC121649
0.8667	High Similarity	NPC52611
0.8667	High Similarity	NPC186227
0.8667	High Similarity	NPC150908
0.8667	High Similarity	NPC99199
0.8667	High Similarity	NPC205026
0.8663	High Similarity	NPC477529
0.8659	High Similarity	NPC207624
0.8659	High Similarity	NPC142308
0.8659	High Similarity	NPC5871
0.8655	High Similarity	NPC53252
0.8639	High Similarity	NPC155640
0.8631	High Similarity	NPC18380
0.8631	High Similarity	NPC175513
0.8623	High Similarity	NPC226287
0.8623	High Similarity	NPC55443
0.8623	High Similarity	NPC51247
0.8623	High Similarity	NPC244750
0.8623	High Similarity	NPC15815
0.8623	High Similarity	NPC18699
0.8623	High Similarity	NPC40583
0.8621	High Similarity	NPC475246
0.8614	High Similarity	NPC32867
0.8614	High Similarity	NPC13879
0.8613	High Similarity	NPC168789
0.8606	High Similarity	NPC71061
0.8606	High Similarity	NPC290830
0.8606	High Similarity	NPC72425
0.8606	High Similarity	NPC303485
0.8606	High Similarity	NPC194593
0.8598	High Similarity	NPC138299
0.8598	High Similarity	NPC111112
0.8598	High Similarity	NPC115324
0.8598	High Similarity	NPC222713
0.8598	High Similarity	NPC58668
0.8598	High Similarity	NPC67322
0.8598	High Similarity	NPC106372
0.8596	High Similarity	NPC47905
0.8596	High Similarity	NPC139683
0.8596	High Similarity	NPC73929
0.8589	High Similarity	NPC226644
0.8589	High Similarity	NPC37226
0.8588	High Similarity	NPC154527
0.8588	High Similarity	NPC469664
0.858	High Similarity	NPC310603
0.858	High Similarity	NPC17816
0.858	High Similarity	NPC150215
0.8571	High Similarity	NPC115432
0.8571	High Similarity	NPC184326
0.8571	High Similarity	NPC155144
0.8571	High Similarity	NPC121647
0.8571	High Similarity	NPC260296
0.8571	High Similarity	NPC292863
0.8571	High Similarity	NPC5671
0.8571	High Similarity	NPC42965
0.8563	High Similarity	NPC3718
0.8563	High Similarity	NPC257166
0.8555	High Similarity	NPC478002
0.8555	High Similarity	NPC477836
0.8555	High Similarity	NPC174700
0.8554	High Similarity	NPC198490
0.8554	High Similarity	NPC66441
0.8554	High Similarity	NPC254351
0.8554	High Similarity	NPC226656
0.8554	High Similarity	NPC79375
0.8554	High Similarity	NPC37253
0.8554	High Similarity	NPC182555
0.8554	High Similarity	NPC66508
0.8539	High Similarity	NPC475220
0.8539	High Similarity	NPC221140
0.8539	High Similarity	NPC226725
0.8539	High Similarity	NPC473686
0.8539	High Similarity	NPC229817
0.8539	High Similarity	NPC475352
0.8539	High Similarity	NPC304322
0.8538	High Similarity	NPC477835
0.8538	High Similarity	NPC224851
0.8531	High Similarity	NPC475662
0.8531	High Similarity	NPC473631
0.8531	High Similarity	NPC293227
0.8531	High Similarity	NPC132111
0.8531	High Similarity	NPC473717
0.8528	High Similarity	NPC135325
0.8521	High Similarity	NPC137232
0.8519	High Similarity	NPC210826
0.8514	High Similarity	NPC46958
0.8514	High Similarity	NPC475233
0.8514	High Similarity	NPC472661
0.8512	High Similarity	NPC474373
0.8512	High Similarity	NPC324736
0.8512	High Similarity	NPC295090
0.8512	High Similarity	NPC195167
0.8506	High Similarity	NPC65885
0.8506	High Similarity	NPC85368
0.8506	High Similarity	NPC470336
0.8506	High Similarity	NPC473834
0.8506	High Similarity	NPC470335
0.8497	Intermediate Similarity	NPC17884
0.8497	Intermediate Similarity	NPC19273
0.8497	Intermediate Similarity	NPC476641
0.8494	Intermediate Similarity	NPC183874
0.8494	Intermediate Similarity	NPC121568

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 NPC59491 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	971
0.2-0.3	1594
0.3-0.4	2677
0.4-0.5	2013
0.5-0.6	1018
0.6-0.7	305
0.7-0.8	150
0.8-0.85	37
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8743	High Similarity	NPD6959	Discontinued
0.8563	High Similarity	NPD3749	Approved
0.8506	High Similarity	NPD6559	Discontinued
0.848	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD8313	Approved
0.8202	Intermediate Similarity	NPD8312	Approved
0.8176	Intermediate Similarity	NPD7768	Phase 2
0.8166	Intermediate Similarity	NPD7819	Suspended
0.8155	Intermediate Similarity	NPD7411	Suspended
0.8129	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD7473	Discontinued
0.8079	Intermediate Similarity	NPD7074	Phase 3
0.8068	Intermediate Similarity	NPD3818	Discontinued
0.8061	Intermediate Similarity	NPD7390	Discontinued
0.8057	Intermediate Similarity	NPD6166	Phase 2
0.8057	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD6232	Discontinued
0.8035	Intermediate Similarity	NPD5494	Approved
0.8023	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7472	Approved
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7808	Phase 3
0.7933	Intermediate Similarity	NPD6797	Phase 2
0.7933	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2344	Approved
0.7892	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7251	Discontinued
0.7882	Intermediate Similarity	NPD4380	Phase 2
0.7866	Intermediate Similarity	NPD1549	Phase 2
0.7861	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3226	Approved
0.7821	Intermediate Similarity	NPD5844	Phase 1
0.7818	Intermediate Similarity	NPD2800	Approved
0.7816	Intermediate Similarity	NPD7075	Discontinued
0.7805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD2533	Approved
0.7798	Intermediate Similarity	NPD2534	Approved
0.7798	Intermediate Similarity	NPD2532	Approved
0.7791	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD1607	Approved
0.7771	Intermediate Similarity	NPD3750	Approved
0.7759	Intermediate Similarity	NPD3882	Suspended
0.7746	Intermediate Similarity	NPD2801	Approved
0.7744	Intermediate Similarity	NPD8151	Discontinued
0.7738	Intermediate Similarity	NPD1511	Approved
0.7725	Intermediate Similarity	NPD2309	Approved
0.7711	Intermediate Similarity	NPD1243	Approved
0.7706	Intermediate Similarity	NPD920	Approved
0.7697	Intermediate Similarity	NPD3926	Phase 2
0.7683	Intermediate Similarity	NPD1510	Phase 2
0.7665	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1240	Approved
0.765	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1512	Approved
0.7644	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD1465	Phase 2
0.7636	Intermediate Similarity	NPD2796	Approved
0.7602	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4287	Approved
0.759	Intermediate Similarity	NPD2346	Discontinued
0.7588	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7697	Approved
0.7577	Intermediate Similarity	NPD7698	Approved
0.7577	Intermediate Similarity	NPD7696	Phase 3
0.7576	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6599	Discontinued
0.7569	Intermediate Similarity	NPD3751	Discontinued
0.7545	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD8455	Phase 2
0.7538	Intermediate Similarity	NPD7871	Phase 2
0.7538	Intermediate Similarity	NPD7870	Phase 2
0.753	Intermediate Similarity	NPD6100	Approved
0.753	Intermediate Similarity	NPD6099	Approved
0.753	Intermediate Similarity	NPD5408	Approved
0.753	Intermediate Similarity	NPD5405	Approved
0.753	Intermediate Similarity	NPD5404	Approved
0.753	Intermediate Similarity	NPD5406	Approved
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7458	Discontinued
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3817	Phase 2
0.7487	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7783	Phase 2
0.7486	Intermediate Similarity	NPD6801	Discontinued
0.7473	Intermediate Similarity	NPD7228	Approved
0.7471	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3748	Approved
0.747	Intermediate Similarity	NPD2799	Discontinued
0.7444	Intermediate Similarity	NPD3787	Discontinued
0.7427	Intermediate Similarity	NPD6799	Approved
0.7425	Intermediate Similarity	NPD2935	Discontinued
0.7425	Intermediate Similarity	NPD1551	Phase 2
0.7424	Intermediate Similarity	NPD7701	Phase 2
0.7414	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5402	Approved
0.7398	Intermediate Similarity	NPD7435	Discontinued
0.7394	Intermediate Similarity	NPD8434	Phase 2
0.7389	Intermediate Similarity	NPD7199	Phase 2
0.7389	Intermediate Similarity	NPD1247	Approved
0.7386	Intermediate Similarity	NPD37	Approved
0.7374	Intermediate Similarity	NPD6234	Discontinued
0.7374	Intermediate Similarity	NPD919	Approved
0.736	Intermediate Similarity	NPD4967	Phase 2
0.736	Intermediate Similarity	NPD4966	Approved
0.736	Intermediate Similarity	NPD4965	Approved
0.7353	Intermediate Similarity	NPD7003	Approved
0.7353	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5710	Approved
0.7348	Intermediate Similarity	NPD5711	Approved
0.7348	Intermediate Similarity	NPD7229	Phase 3
0.732	Intermediate Similarity	NPD7699	Phase 2
0.732	Intermediate Similarity	NPD7700	Phase 2
0.7317	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7801	Approved
0.7308	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD8150	Discontinued
0.7301	Intermediate Similarity	NPD4908	Phase 1
0.7284	Intermediate Similarity	NPD2798	Approved
0.7283	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8320	Phase 1
0.7273	Intermediate Similarity	NPD8319	Approved
0.7264	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7874	Approved
0.7259	Intermediate Similarity	NPD6823	Phase 2
0.7258	Intermediate Similarity	NPD5953	Discontinued
0.7254	Intermediate Similarity	NPD6535	Approved
0.7254	Intermediate Similarity	NPD6534	Approved
0.7246	Intermediate Similarity	NPD6651	Approved
0.7225	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2313	Discontinued
0.7207	Intermediate Similarity	NPD2296	Approved
0.72	Intermediate Similarity	NPD5403	Approved
0.7189	Intermediate Similarity	NPD7177	Discontinued
0.7184	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1471	Phase 3
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7151	Intermediate Similarity	NPD7286	Phase 2
0.7151	Intermediate Similarity	NPD5760	Phase 2
0.7151	Intermediate Similarity	NPD4628	Phase 3
0.7151	Intermediate Similarity	NPD5761	Phase 2
0.7128	Intermediate Similarity	NPD7240	Approved
0.7126	Intermediate Similarity	NPD943	Approved
0.7108	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3764	Approved
0.7099	Intermediate Similarity	NPD4749	Approved
0.7086	Intermediate Similarity	NPD5401	Approved
0.7045	Intermediate Similarity	NPD6273	Approved
0.7037	Intermediate Similarity	NPD7685	Pre-registration
0.7026	Intermediate Similarity	NPD6212	Phase 3
0.7026	Intermediate Similarity	NPD6213	Phase 3
0.7026	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1203	Approved
0.7012	Intermediate Similarity	NPD1470	Approved
0.7006	Intermediate Similarity	NPD3268	Approved
0.7005	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4360	Phase 2
0.699	Remote Similarity	NPD4363	Phase 3
0.6965	Remote Similarity	NPD7680	Approved
0.6959	Remote Similarity	NPD4308	Phase 3
0.6946	Remote Similarity	NPD7584	Approved
0.6933	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD4288	Approved
0.6919	Remote Similarity	NPD8366	Approved
0.6909	Remote Similarity	NPD2797	Approved
0.6906	Remote Similarity	NPD6279	Approved
0.6906	Remote Similarity	NPD6280	Approved
0.6905	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD411	Approved
0.6902	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6832	Phase 2
0.6882	Remote Similarity	NPD447	Suspended
0.6882	Remote Similarity	NPD6808	Phase 2
0.6882	Remote Similarity	NPD1933	Approved
0.6871	Remote Similarity	NPD1201	Approved
0.6871	Remote Similarity	NPD1610	Phase 2
0.6869	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4361	Phase 2
0.6851	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8059	Phase 3
0.6837	Remote Similarity	NPD8058	Clinical (unspecified phase)

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