NPASS Compound

Structure

NPC470919 OpenBabel07101719152D 34 38 0 0 1 0 0 0 0 0999 V2000 6.7009 0.1909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8511 -0.2040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7315 0.4729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3121 1.8219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4554 1.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0675 0.8932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9125 1.8915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0934 -0.4729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5559 -0.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1426 0.6957 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9125 0.9457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7818 0.7101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0934 0.4729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0934 2.3644 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2744 -0.9457 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9034 0.0400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3679 0.1033 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1821 1.0328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2744 1.8915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5091 1.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7069 -0.2203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4554 0.4729 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2744 0.9457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4554 -0.4729 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5559 0.7651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0934 3.3101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2245 1.9776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4554 2.3644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8005 2.2977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5921 0.1128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1775 1.3623 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 2.6653 -0.6872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6593 1.0030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 32 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 23 1 6 0 0 0 14 19 1 0 0 0 0 14 26 1 1 0 0 0 15 24 1 6 0 0 0 15 33 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 21 1 0 0 0 0 17 34 1 1 0 0 0 18 25 1 6 0 0 0 18 27 1 0 0 0 0 19 23 1 6 0 0 0 19 28 1 0 0 0 0 20 29 2 0 0 0 0 20 34 1 0 0 0 0 21 30 2 0 0 0 0 21 33 1 0 0 0 0 22 23 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 5 1 6 0 0 0 24 9 1 1 0 0 0 25 31 1 1 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.22
Volume:	466.74
LogP:	2.085
LogD:	0.829
LogS:	-3.85
# Rotatable Bonds:	4
TPSA:	142.75
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.336
Synthetic Accessibility Score:	6.698
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.611
MDCK Permeability:	8.908885502023622e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.791

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	57.12436294555664%
Volume Distribution (VD):	0.703
Pgp-substrate:	52.768768310546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.8
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.259
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	4.431
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.79
Drug-inuced Liver Injury (DILI):	0.433
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.447
Maximum Recommended Daily Dose:	0.401
Skin Sensitization:	0.136
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC470919

Natural Product ID:	NPC470919
*Common Name:**	Altissinol B
IUPAC Name:	n.a.
Synonyms:	Altissinol B
Standard InCHIKey:	WGNVNSPRXOUTKL-WCZQPVQQSA-N
Standard InCHI:	InChI=1S/C25H34O9/c1-6-10(2)20(29)34-17-16-12(4)18(27)25(31)22-23(5)13(11(3)7-14(26)19(23)28)8-15(33-21(17)30)24(16,22)9-32-25/h7,10,13-19,22,26-28,31H,4,6,8-9H2,1-3,5H3/t10?,13-,14-,15+,16+,17+,18+,19+,22+,23+,24-,25+/m0/s1
SMILES:	CCC(C)C(=O)OC1C2C(=C)C(C3(C4C2(CO3)C(CC5C4(C(C(C=C5C)O)O)C)OC1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2314659
PubChem CID:	71519984
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	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	2
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	>	50000.0	nM	PMID[466261]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1220.0	nM	PMID[466261]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2360.0	nM	PMID[466261]

☑ 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 NPC470919 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	236
0.1-0.2	1369
0.2-0.3	3961
0.3-0.4	7567
0.4-0.5	12494
0.5-0.6	7350
0.6-0.7	5355
0.7-0.8	3798
0.8-0.85	467
0.85-0.9	60
0.9-0.95	31
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469877
0.9906	High Similarity	NPC470628
0.9906	High Similarity	NPC259306
0.9906	High Similarity	NPC474046
0.981	High Similarity	NPC302146
0.9537	High Similarity	NPC474734
0.9524	High Similarity	NPC472534
0.9524	High Similarity	NPC143706
0.9444	High Similarity	NPC18547
0.9444	High Similarity	NPC474906
0.9369	High Similarity	NPC109607
0.9369	High Similarity	NPC107338
0.9358	High Similarity	NPC235539
0.9358	High Similarity	NPC134869
0.9358	High Similarity	NPC152199
0.9352	High Similarity	NPC51978
0.9279	High Similarity	NPC475775
0.9279	High Similarity	NPC476529
0.9273	High Similarity	NPC473590
0.9273	High Similarity	NPC473968
0.9259	High Similarity	NPC289312
0.9259	High Similarity	NPC11252
0.9211	High Similarity	NPC470922
0.9189	High Similarity	NPC297179
0.9189	High Similarity	NPC470776
0.9167	High Similarity	NPC201992
0.9107	High Similarity	NPC122971
0.9099	High Similarity	NPC470775
0.9099	High Similarity	NPC176513
0.9027	High Similarity	NPC112038
0.9009	High Similarity	NPC96312
0.9009	High Similarity	NPC40632
0.9009	High Similarity	NPC328374
0.9009	High Similarity	NPC251236
0.8981	High Similarity	NPC141350
0.8957	High Similarity	NPC67251
0.8919	High Similarity	NPC472274
0.8919	High Similarity	NPC473798
0.8889	High Similarity	NPC293850
0.885	High Similarity	NPC188667
0.885	High Similarity	NPC204552
0.8829	High Similarity	NPC49451
0.8796	High Similarity	NPC230541
0.8761	High Similarity	NPC309433
0.8729	High Similarity	NPC470780
0.8718	High Similarity	NPC476729
0.8684	High Similarity	NPC251310
0.8684	High Similarity	NPC17772
0.8673	High Similarity	NPC179626
0.8632	High Similarity	NPC18945
0.8632	High Similarity	NPC478066
0.8632	High Similarity	NPC91693
0.8632	High Similarity	NPC105926
0.8632	High Similarity	NPC265557
0.8624	High Similarity	NPC293512
0.8624	High Similarity	NPC3316
0.8624	High Similarity	NPC144854
0.8621	High Similarity	NPC477046
0.8621	High Similarity	NPC102822
0.8609	High Similarity	NPC469488
0.8596	High Similarity	NPC474654
0.8596	High Similarity	NPC470854
0.8596	High Similarity	NPC97908
0.8596	High Similarity	NPC122033
0.8596	High Similarity	NPC287343
0.8596	High Similarity	NPC470171
0.8584	High Similarity	NPC475633
0.8571	High Similarity	NPC174836
0.8571	High Similarity	NPC474516
0.8559	High Similarity	NPC24651
0.8559	High Similarity	NPC470477
0.8547	High Similarity	NPC249848
0.8547	High Similarity	NPC312833
0.8547	High Similarity	NPC235438
0.8547	High Similarity	NPC40775
0.8547	High Similarity	NPC107966
0.8545	High Similarity	NPC277017
0.8545	High Similarity	NPC154608
0.8545	High Similarity	NPC192813
0.8532	High Similarity	NPC127609
0.8522	High Similarity	NPC286347
0.8512	High Similarity	NPC262796
0.8512	High Similarity	NPC329993
0.8512	High Similarity	NPC134914
0.8512	High Similarity	NPC172374
0.8512	High Similarity	NPC475377
0.8512	High Similarity	NPC173435
0.8512	High Similarity	NPC45346
0.8512	High Similarity	NPC475167
0.8512	High Similarity	NPC264566
0.8512	High Similarity	NPC478065
0.8512	High Similarity	NPC301639
0.8512	High Similarity	NPC478064
0.8512	High Similarity	NPC476074
0.85	High Similarity	NPC188291
0.8496	Intermediate Similarity	NPC7921
0.8496	Intermediate Similarity	NPC208998
0.8482	Intermediate Similarity	NPC250481
0.8482	Intermediate Similarity	NPC263827
0.8482	Intermediate Similarity	NPC285410
0.8475	Intermediate Similarity	NPC235405
0.8475	Intermediate Similarity	NPC30735
0.8475	Intermediate Similarity	NPC281148
0.8462	Intermediate Similarity	NPC75417
0.8462	Intermediate Similarity	NPC202051
0.8462	Intermediate Similarity	NPC470779
0.8448	Intermediate Similarity	NPC309780
0.8448	Intermediate Similarity	NPC469945
0.8448	Intermediate Similarity	NPC11551
0.8448	Intermediate Similarity	NPC39211
0.8448	Intermediate Similarity	NPC114441
0.8448	Intermediate Similarity	NPC157868
0.8448	Intermediate Similarity	NPC473884
0.8448	Intermediate Similarity	NPC475171
0.8448	Intermediate Similarity	NPC214484
0.8448	Intermediate Similarity	NPC208381
0.8448	Intermediate Similarity	NPC180550
0.8448	Intermediate Similarity	NPC192791
0.8448	Intermediate Similarity	NPC470777
0.8448	Intermediate Similarity	NPC6377
0.8448	Intermediate Similarity	NPC35405
0.8448	Intermediate Similarity	NPC472949
0.8443	Intermediate Similarity	NPC478153
0.8443	Intermediate Similarity	NPC478152
0.8443	Intermediate Similarity	NPC478150
0.8443	Intermediate Similarity	NPC102316
0.844	Intermediate Similarity	NPC258532
0.844	Intermediate Similarity	NPC475036
0.8435	Intermediate Similarity	NPC471547
0.8435	Intermediate Similarity	NPC224121
0.8421	Intermediate Similarity	NPC117712
0.8421	Intermediate Similarity	NPC181145
0.8421	Intermediate Similarity	NPC243354
0.8407	Intermediate Similarity	NPC116794
0.8407	Intermediate Similarity	NPC472002
0.8393	Intermediate Similarity	NPC220984
0.8393	Intermediate Similarity	NPC110139
0.8393	Intermediate Similarity	NPC274507
0.8393	Intermediate Similarity	NPC199457
0.8393	Intermediate Similarity	NPC75747
0.8393	Intermediate Similarity	NPC83005
0.8393	Intermediate Similarity	NPC108709
0.8393	Intermediate Similarity	NPC68419
0.8393	Intermediate Similarity	NPC102914
0.8393	Intermediate Similarity	NPC7870
0.839	Intermediate Similarity	NPC473231
0.839	Intermediate Similarity	NPC222688
0.839	Intermediate Similarity	NPC213952
0.8376	Intermediate Similarity	NPC471406
0.8376	Intermediate Similarity	NPC472257
0.8376	Intermediate Similarity	NPC294112
0.8374	Intermediate Similarity	NPC478151
0.8364	Intermediate Similarity	NPC102352
0.8362	Intermediate Similarity	NPC276758
0.8362	Intermediate Similarity	NPC18233
0.8361	Intermediate Similarity	NPC478155
0.8361	Intermediate Similarity	NPC477197
0.8361	Intermediate Similarity	NPC25998
0.8348	Intermediate Similarity	NPC16081
0.8348	Intermediate Similarity	NPC173686
0.8347	Intermediate Similarity	NPC329923
0.8347	Intermediate Similarity	NPC477078
0.8347	Intermediate Similarity	NPC477075
0.8347	Intermediate Similarity	NPC475281
0.8333	Intermediate Similarity	NPC225049
0.8333	Intermediate Similarity	NPC194273
0.8333	Intermediate Similarity	NPC269315
0.8333	Intermediate Similarity	NPC271138
0.8333	Intermediate Similarity	NPC285091
0.8333	Intermediate Similarity	NPC470218
0.8333	Intermediate Similarity	NPC474410
0.8333	Intermediate Similarity	NPC311592
0.8333	Intermediate Similarity	NPC293658
0.8333	Intermediate Similarity	NPC75167
0.832	Intermediate Similarity	NPC251998
0.8319	Intermediate Similarity	NPC146945
0.8319	Intermediate Similarity	NPC171888
0.8319	Intermediate Similarity	NPC30397
0.8319	Intermediate Similarity	NPC108748
0.8319	Intermediate Similarity	NPC179434
0.8319	Intermediate Similarity	NPC191763
0.8319	Intermediate Similarity	NPC188738
0.8319	Intermediate Similarity	NPC157476
0.8319	Intermediate Similarity	NPC257211
0.8319	Intermediate Similarity	NPC473481
0.8319	Intermediate Similarity	NPC227397
0.8319	Intermediate Similarity	NPC471243
0.8319	Intermediate Similarity	NPC211798
0.8319	Intermediate Similarity	NPC235841
0.8319	Intermediate Similarity	NPC475668
0.8319	Intermediate Similarity	NPC475480
0.8319	Intermediate Similarity	NPC297208
0.8319	Intermediate Similarity	NPC473921
0.8306	Intermediate Similarity	NPC15215
0.8306	Intermediate Similarity	NPC242486
0.8305	Intermediate Similarity	NPC223301
0.8305	Intermediate Similarity	NPC104372
0.8305	Intermediate Similarity	NPC22956
0.8305	Intermediate Similarity	NPC86222
0.8305	Intermediate Similarity	NPC31193

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 NPC470919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1556
0.2-0.3	3705
0.3-0.4	2357
0.4-0.5	760
0.5-0.6	308
0.6-0.7	158
0.7-0.8	107
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
0.8276	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD8328	Phase 3
0.7982	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6686	Approved
0.7886	Intermediate Similarity	NPD7507	Approved
0.7805	Intermediate Similarity	NPD7492	Approved
0.7778	Intermediate Similarity	NPD6882	Approved
0.7778	Intermediate Similarity	NPD8297	Approved
0.7769	Intermediate Similarity	NPD6319	Approved
0.7769	Intermediate Similarity	NPD6054	Approved
0.7769	Intermediate Similarity	NPD6059	Approved
0.776	Intermediate Similarity	NPD7736	Approved
0.7742	Intermediate Similarity	NPD6616	Approved
0.7739	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7128	Approved
0.7719	Intermediate Similarity	NPD5739	Approved
0.7719	Intermediate Similarity	NPD6675	Approved
0.7719	Intermediate Similarity	NPD6402	Approved
0.7705	Intermediate Similarity	NPD8517	Approved
0.7705	Intermediate Similarity	NPD8515	Approved
0.7705	Intermediate Similarity	NPD8516	Approved
0.7705	Intermediate Similarity	NPD8513	Phase 3
0.7698	Intermediate Similarity	NPD7319	Approved
0.768	Intermediate Similarity	NPD8293	Discontinued
0.768	Intermediate Similarity	NPD7078	Approved
0.7672	Intermediate Similarity	NPD6373	Approved
0.7672	Intermediate Similarity	NPD6372	Approved
0.7667	Intermediate Similarity	NPD6009	Approved
0.7652	Intermediate Similarity	NPD6412	Phase 2
0.7642	Intermediate Similarity	NPD6370	Approved
0.7586	Intermediate Similarity	NPD6899	Approved
0.7586	Intermediate Similarity	NPD6881	Approved
0.7586	Intermediate Similarity	NPD7320	Approved
0.7563	Intermediate Similarity	NPD4632	Approved
0.7561	Intermediate Similarity	NPD6016	Approved
0.7561	Intermediate Similarity	NPD6015	Approved
0.7542	Intermediate Similarity	NPD6650	Approved
0.7542	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6649	Approved
0.7521	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD5988	Approved
0.75	Intermediate Similarity	NPD5697	Approved
0.7458	Intermediate Similarity	NPD7102	Approved
0.7458	Intermediate Similarity	NPD6883	Approved
0.7458	Intermediate Similarity	NPD7290	Approved
0.7434	Intermediate Similarity	NPD7640	Approved
0.7434	Intermediate Similarity	NPD7639	Approved
0.7417	Intermediate Similarity	NPD8133	Approved
0.7398	Intermediate Similarity	NPD7516	Approved
0.7395	Intermediate Similarity	NPD8130	Phase 1
0.7395	Intermediate Similarity	NPD6847	Approved
0.7395	Intermediate Similarity	NPD6869	Approved
0.7395	Intermediate Similarity	NPD6617	Approved
0.7377	Intermediate Similarity	NPD7115	Discovery
0.7373	Intermediate Similarity	NPD6014	Approved
0.7373	Intermediate Similarity	NPD6013	Approved
0.7373	Intermediate Similarity	NPD6012	Approved
0.7345	Intermediate Similarity	NPD4225	Approved
0.7345	Intermediate Similarity	NPD7638	Approved
0.7317	Intermediate Similarity	NPD7327	Approved
0.7317	Intermediate Similarity	NPD7328	Approved
0.7311	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7604	Phase 2
0.7288	Intermediate Similarity	NPD6011	Approved
0.728	Intermediate Similarity	NPD8033	Approved
0.728	Intermediate Similarity	NPD5983	Phase 2
0.7266	Intermediate Similarity	NPD8074	Phase 3
0.725	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6033	Approved
0.7207	Intermediate Similarity	NPD5779	Approved
0.7207	Intermediate Similarity	NPD6399	Phase 3
0.7207	Intermediate Similarity	NPD5778	Approved
0.72	Intermediate Similarity	NPD8294	Approved
0.72	Intermediate Similarity	NPD8377	Approved
0.7188	Intermediate Similarity	NPD6336	Discontinued
0.7155	Intermediate Similarity	NPD5211	Phase 2
0.7143	Intermediate Similarity	NPD8380	Approved
0.7143	Intermediate Similarity	NPD8335	Approved
0.7143	Intermediate Similarity	NPD7503	Approved
0.7143	Intermediate Similarity	NPD8379	Approved
0.7143	Intermediate Similarity	NPD8296	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD6921	Approved
0.7143	Intermediate Similarity	NPD8378	Approved
0.7119	Intermediate Similarity	NPD6008	Approved
0.7117	Intermediate Similarity	NPD7983	Approved
0.7117	Intermediate Similarity	NPD7515	Phase 2
0.7117	Intermediate Similarity	NPD6411	Approved
0.7105	Intermediate Similarity	NPD6084	Phase 2
0.7105	Intermediate Similarity	NPD6083	Phase 2
0.7105	Intermediate Similarity	NPD4755	Approved
0.7105	Intermediate Similarity	NPD7902	Approved
0.7059	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5141	Approved
0.7027	Intermediate Similarity	NPD46	Approved
0.7027	Intermediate Similarity	NPD6698	Approved
0.7025	Intermediate Similarity	NPD4634	Approved
0.7016	Intermediate Similarity	NPD6274	Approved
0.6984	Remote Similarity	NPD7101	Approved
0.6984	Remote Similarity	NPD7100	Approved
0.6983	Remote Similarity	NPD5286	Approved
0.6983	Remote Similarity	NPD5285	Approved
0.6983	Remote Similarity	NPD4700	Approved
0.6983	Remote Similarity	NPD4696	Approved
0.6937	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5328	Approved
0.6937	Remote Similarity	NPD6101	Approved
0.6905	Remote Similarity	NPD6335	Approved
0.688	Remote Similarity	NPD6868	Approved
0.6875	Remote Similarity	NPD6908	Approved
0.6875	Remote Similarity	NPD6909	Approved
0.687	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5222	Approved
0.687	Remote Similarity	NPD5221	Approved
0.687	Remote Similarity	NPD4697	Phase 3
0.6864	Remote Similarity	NPD5224	Approved
0.6864	Remote Similarity	NPD7632	Discontinued
0.6864	Remote Similarity	NPD5225	Approved
0.6864	Remote Similarity	NPD4633	Approved
0.6864	Remote Similarity	NPD5226	Approved
0.6847	Remote Similarity	NPD5737	Approved
0.6847	Remote Similarity	NPD6672	Approved
0.6842	Remote Similarity	NPD7900	Approved
0.6842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4768	Approved
0.6833	Remote Similarity	NPD4767	Approved
0.6825	Remote Similarity	NPD6317	Approved
0.6814	Remote Similarity	NPD8034	Phase 2
0.6814	Remote Similarity	NPD6079	Approved
0.6814	Remote Similarity	NPD8035	Phase 2
0.681	Remote Similarity	NPD5173	Approved
0.6807	Remote Similarity	NPD5175	Approved
0.6807	Remote Similarity	NPD5174	Approved
0.6791	Remote Similarity	NPD7260	Phase 2
0.6789	Remote Similarity	NPD4786	Approved
0.6783	Remote Similarity	NPD5695	Phase 3
0.678	Remote Similarity	NPD5223	Approved
0.678	Remote Similarity	NPD5344	Discontinued
0.6774	Remote Similarity	NPD6053	Discontinued
0.6772	Remote Similarity	NPD6313	Approved
0.6772	Remote Similarity	NPD6314	Approved
0.6769	Remote Similarity	NPD6067	Discontinued
0.6759	Remote Similarity	NPD3667	Approved
0.6757	Remote Similarity	NPD3573	Approved
0.6752	Remote Similarity	NPD5696	Approved
0.675	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7839	Suspended
0.6721	Remote Similarity	NPD4730	Approved
0.6721	Remote Similarity	NPD4729	Approved
0.6715	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD7637	Suspended
0.6639	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6845	Suspended
0.6615	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5249	Phase 3
0.6613	Remote Similarity	NPD5247	Approved
0.6613	Remote Similarity	NPD5251	Approved
0.6613	Remote Similarity	NPD5250	Approved
0.6613	Remote Similarity	NPD5248	Approved
0.6607	Remote Similarity	NPD7524	Approved
0.6585	Remote Similarity	NPD5128	Approved
0.6549	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8415	Approved
0.6518	Remote Similarity	NPD6409	Approved
0.6518	Remote Similarity	NPD7146	Approved
0.6518	Remote Similarity	NPD6684	Approved
0.6518	Remote Similarity	NPD7521	Approved
0.6518	Remote Similarity	NPD5330	Approved
0.6518	Remote Similarity	NPD6098	Approved
0.6518	Remote Similarity	NPD7334	Approved
0.6491	Remote Similarity	NPD4753	Phase 2
0.6491	Remote Similarity	NPD6080	Approved
0.6491	Remote Similarity	NPD6673	Approved
0.6491	Remote Similarity	NPD6904	Approved
0.6491	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7645	Phase 2
0.648	Remote Similarity	NPD6371	Approved
0.6471	Remote Similarity	NPD5956	Approved
0.6471	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4202	Approved
0.6429	Remote Similarity	NPD5215	Approved
0.6429	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5217	Approved
0.6429	Remote Similarity	NPD5216	Approved
0.6417	Remote Similarity	NPD6648	Approved
0.641	Remote Similarity	NPD5282	Discontinued
0.6404	Remote Similarity	NPD6903	Approved
0.6396	Remote Similarity	NPD6110	Phase 1
0.6379	Remote Similarity	NPD5693	Phase 1
0.6356	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5169	Approved
0.6349	Remote Similarity	NPD5135	Approved
0.6339	Remote Similarity	NPD3666	Approved
0.6339	Remote Similarity	NPD3668	Phase 3
0.6339	Remote Similarity	NPD7338	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