NPASS Compound

Structure

NPC470628 OpenBabel07101719512D 35 39 0 0 1 0 0 0 0 0999 V2000 5.4929 -0.9076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7387 0.4736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3171 1.8246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0514 0.4049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4576 1.4208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8585 -0.2043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9184 1.8944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.4736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5567 -0.7663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9184 0.9472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7845 0.7111 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0981 0.4736 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0981 2.3679 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2778 -0.9472 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.9063 0.0400 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.3714 0.1035 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.1839 1.0343 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2778 1.8944 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7110 -0.2206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4576 0.4736 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5159 1.4001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1503 0.6968 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.2778 0.9472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4576 -0.4736 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5567 0.7663 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0981 3.3151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2264 1.9806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4576 2.3679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5975 0.1130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8078 2.3012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8537 1.3312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1777 1.3644 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 2.6694 -0.6882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6633 1.0046 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 4 22 1 0 0 0 0 6 22 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 24 1 0 0 0 0 9 33 1 0 0 0 0 10 12 1 0 0 0 0 11 3 1 6 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 23 1 0 0 0 0 13 18 1 0 0 0 0 13 26 1 1 0 0 0 14 24 1 0 0 0 0 14 34 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 16 35 1 0 0 0 0 17 25 1 6 0 0 0 17 27 1 0 0 0 0 18 23 1 6 0 0 0 18 28 1 0 0 0 0 19 29 2 0 0 0 0 19 34 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 30 2 0 0 0 0 21 35 1 0 0 0 0 22 31 1 0 0 0 0 23 5 1 6 0 0 0 25 32 1 1 0 0 0 25 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.23
Volume:	478.167
LogP:	1.234
LogD:	0.695
LogS:	-3.47
# Rotatable Bonds:	4
TPSA:	162.98
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	6.785
Fsp3:	0.84
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:	-5.421
MDCK Permeability:	9.149224933935329e-05
Pgp-inhibitor:	0.797
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.186
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	47.718963623046875%
Volume Distribution (VD):	0.71
Pgp-substrate:	37.48414611816406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.641
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.122
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	2.199
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.605
Drug-inuced Liver Injury (DILI):	0.509
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.022
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.619

Download Data

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

Natural Product: NPC470628

Natural Product ID:	NPC470628
*Common Name:**	Glaucarubin
IUPAC Name:	n.a.
Synonyms:	Glaucarubin; Glaumeba
Standard InCHIKey:	LZKVXMYVBSNXER-DCNWDFLTSA-N
Standard InCHI:	InChI=1S/C25H36O10/c1-6-22(4,31)21(30)35-16-15-11(3)17(27)25(32)20-23(5)12(10(2)7-13(26)18(23)28)8-14(34-19(16)29)24(15,20)9-33-25/h7,11-18,20,26-28,31-32H,6,8-9H2,1-5H3/t11-,12?,13+,14?,15?,16?,17-,18-,20?,22?,23-,24?,25-/m1/s1
SMILES:	CCC(C(=O)OC1C(=O)OC2C34C1[C@@H](C)[C@@H](O)[C@](C4[C@@]1(C(C2)C(=C[C@@H]([C@H]1O)O)C)C)(OC3)O)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2106871
PubChem CID:	15063
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	4

Activity Type	# Activity
Cell Line	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000	nM	PMID[23675610]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	35570	nM	PMID[23273047]
NPT2	Others	Unspecified		IC50	=	23460	nM	PMID[23493449]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	1.57	ug/ml	PMID[15787435]

☑ 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 NPC470628 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	242
0.1-0.2	1394
0.2-0.3	4002
0.3-0.4	7635
0.4-0.5	12408
0.5-0.6	7192
0.6-0.7	5443
0.7-0.8	3820
0.8-0.85	458
0.85-0.9	57
0.9-0.95	37
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474046
1.0	High Similarity	NPC259306
0.9906	High Similarity	NPC470919
0.9906	High Similarity	NPC469877
0.9717	High Similarity	NPC302146
0.963	High Similarity	NPC474734
0.945	High Similarity	NPC152199
0.945	High Similarity	NPC235539
0.945	High Similarity	NPC134869
0.9434	High Similarity	NPC143706
0.9434	High Similarity	NPC472534
0.9364	High Similarity	NPC473590
0.9358	High Similarity	NPC474906
0.9358	High Similarity	NPC18547
0.9298	High Similarity	NPC470922
0.9286	High Similarity	NPC109607
0.9286	High Similarity	NPC107338
0.9279	High Similarity	NPC470776
0.9279	High Similarity	NPC297179
0.9266	High Similarity	NPC51978
0.9196	High Similarity	NPC475775
0.9196	High Similarity	NPC476529
0.9189	High Similarity	NPC473968
0.9189	High Similarity	NPC176513
0.9189	High Similarity	NPC470775
0.9174	High Similarity	NPC289312
0.9174	High Similarity	NPC11252
0.9115	High Similarity	NPC112038
0.9099	High Similarity	NPC328374
0.9099	High Similarity	NPC40632
0.9099	High Similarity	NPC96312
0.9099	High Similarity	NPC251236
0.9083	High Similarity	NPC201992
0.9043	High Similarity	NPC67251
0.9027	High Similarity	NPC122971
0.9009	High Similarity	NPC473798
0.8938	High Similarity	NPC204552
0.8938	High Similarity	NPC188667
0.8919	High Similarity	NPC49451
0.8899	High Similarity	NPC141350
0.8839	High Similarity	NPC472274
0.8814	High Similarity	NPC470780
0.8807	High Similarity	NPC293850
0.8803	High Similarity	NPC476729
0.8772	High Similarity	NPC17772
0.8772	High Similarity	NPC251310
0.8761	High Similarity	NPC179626
0.8718	High Similarity	NPC91693
0.8718	High Similarity	NPC18945
0.8718	High Similarity	NPC105926
0.8718	High Similarity	NPC265557
0.8716	High Similarity	NPC230541
0.8707	High Similarity	NPC477046
0.8707	High Similarity	NPC102822
0.8696	High Similarity	NPC469488
0.8684	High Similarity	NPC287343
0.8684	High Similarity	NPC470854
0.8684	High Similarity	NPC309433
0.8684	High Similarity	NPC97908
0.8684	High Similarity	NPC474654
0.8684	High Similarity	NPC122033
0.8661	High Similarity	NPC474516
0.8661	High Similarity	NPC174836
0.8644	High Similarity	NPC24651
0.8632	High Similarity	NPC312833
0.8624	High Similarity	NPC127609
0.8584	High Similarity	NPC208998
0.8584	High Similarity	NPC7921
0.8583	High Similarity	NPC188291
0.8559	High Similarity	NPC478066
0.8547	High Similarity	NPC470779
0.8547	High Similarity	NPC75417
0.8545	High Similarity	NPC144854
0.8545	High Similarity	NPC3316
0.8545	High Similarity	NPC293512
0.8534	High Similarity	NPC470777
0.8532	High Similarity	NPC475036
0.8532	High Similarity	NPC258532
0.8525	High Similarity	NPC102316
0.8522	High Similarity	NPC470171
0.8509	High Similarity	NPC475633
0.8509	High Similarity	NPC181145
0.8509	High Similarity	NPC117712
0.8496	Intermediate Similarity	NPC472002
0.8487	Intermediate Similarity	NPC470477
0.8475	Intermediate Similarity	NPC473231
0.8475	Intermediate Similarity	NPC249848
0.8475	Intermediate Similarity	NPC222688
0.8475	Intermediate Similarity	NPC40775
0.8475	Intermediate Similarity	NPC235438
0.8475	Intermediate Similarity	NPC107966
0.8468	Intermediate Similarity	NPC192813
0.8468	Intermediate Similarity	NPC277017
0.8468	Intermediate Similarity	NPC154608
0.8462	Intermediate Similarity	NPC471406
0.8455	Intermediate Similarity	NPC478151
0.8448	Intermediate Similarity	NPC276758
0.8448	Intermediate Similarity	NPC286347
0.8448	Intermediate Similarity	NPC18233
0.8443	Intermediate Similarity	NPC264566
0.8443	Intermediate Similarity	NPC478064
0.8443	Intermediate Similarity	NPC478065
0.8443	Intermediate Similarity	NPC173435
0.8443	Intermediate Similarity	NPC329993
0.8443	Intermediate Similarity	NPC301639
0.8443	Intermediate Similarity	NPC475167
0.8443	Intermediate Similarity	NPC262796
0.8443	Intermediate Similarity	NPC134914
0.8443	Intermediate Similarity	NPC475377
0.8443	Intermediate Similarity	NPC172374
0.8443	Intermediate Similarity	NPC476074
0.8443	Intermediate Similarity	NPC45346
0.8435	Intermediate Similarity	NPC173686
0.8435	Intermediate Similarity	NPC16081
0.8421	Intermediate Similarity	NPC311592
0.8421	Intermediate Similarity	NPC271138
0.8421	Intermediate Similarity	NPC269315
0.8421	Intermediate Similarity	NPC75167
0.8417	Intermediate Similarity	NPC225049
0.8407	Intermediate Similarity	NPC263827
0.8407	Intermediate Similarity	NPC285410
0.8407	Intermediate Similarity	NPC250481
0.8407	Intermediate Similarity	NPC157476
0.8407	Intermediate Similarity	NPC475668
0.8407	Intermediate Similarity	NPC146945
0.8407	Intermediate Similarity	NPC475480
0.8407	Intermediate Similarity	NPC171888
0.8407	Intermediate Similarity	NPC473921
0.8403	Intermediate Similarity	NPC281148
0.8403	Intermediate Similarity	NPC30735
0.8403	Intermediate Similarity	NPC235405
0.8403	Intermediate Similarity	NPC227397
0.84	Intermediate Similarity	NPC251998
0.8393	Intermediate Similarity	NPC218853
0.839	Intermediate Similarity	NPC473250
0.839	Intermediate Similarity	NPC202051
0.8387	Intermediate Similarity	NPC15215
0.8387	Intermediate Similarity	NPC242486
0.8376	Intermediate Similarity	NPC35405
0.8376	Intermediate Similarity	NPC39211
0.8376	Intermediate Similarity	NPC11551
0.8376	Intermediate Similarity	NPC469945
0.8376	Intermediate Similarity	NPC6377
0.8376	Intermediate Similarity	NPC192791
0.8376	Intermediate Similarity	NPC477071
0.8376	Intermediate Similarity	NPC473884
0.8376	Intermediate Similarity	NPC268958
0.8376	Intermediate Similarity	NPC472949
0.8376	Intermediate Similarity	NPC114441
0.8376	Intermediate Similarity	NPC309780
0.8376	Intermediate Similarity	NPC208381
0.8376	Intermediate Similarity	NPC180550
0.8376	Intermediate Similarity	NPC157868
0.8376	Intermediate Similarity	NPC214484
0.8376	Intermediate Similarity	NPC475171
0.8374	Intermediate Similarity	NPC478153
0.8374	Intermediate Similarity	NPC478154
0.8374	Intermediate Similarity	NPC478150
0.8374	Intermediate Similarity	NPC471855
0.8374	Intermediate Similarity	NPC478152
0.8362	Intermediate Similarity	NPC477116
0.8362	Intermediate Similarity	NPC471547
0.8362	Intermediate Similarity	NPC224121
0.8362	Intermediate Similarity	NPC27999
0.8348	Intermediate Similarity	NPC220293
0.8348	Intermediate Similarity	NPC45218
0.8348	Intermediate Similarity	NPC323821
0.8348	Intermediate Similarity	NPC143268
0.8348	Intermediate Similarity	NPC268238
0.8348	Intermediate Similarity	NPC243354
0.8347	Intermediate Similarity	NPC476008
0.8347	Intermediate Similarity	NPC470882
0.8333	Intermediate Similarity	NPC295885
0.8333	Intermediate Similarity	NPC280782
0.8333	Intermediate Similarity	NPC130427
0.8333	Intermediate Similarity	NPC46388
0.8333	Intermediate Similarity	NPC116794
0.8333	Intermediate Similarity	NPC596
0.8333	Intermediate Similarity	NPC269530
0.8333	Intermediate Similarity	NPC140045
0.8333	Intermediate Similarity	NPC23275
0.8333	Intermediate Similarity	NPC37739
0.832	Intermediate Similarity	NPC262813
0.8319	Intermediate Similarity	NPC475563
0.8319	Intermediate Similarity	NPC475134
0.8319	Intermediate Similarity	NPC75747
0.8319	Intermediate Similarity	NPC108709
0.8319	Intermediate Similarity	NPC110139
0.8319	Intermediate Similarity	NPC28532
0.8319	Intermediate Similarity	NPC274507
0.8319	Intermediate Similarity	NPC68419
0.8319	Intermediate Similarity	NPC199457
0.8319	Intermediate Similarity	NPC83005
0.8319	Intermediate Similarity	NPC220984
0.8319	Intermediate Similarity	NPC213952
0.8319	Intermediate Similarity	NPC102914
0.8319	Intermediate Similarity	NPC7870
0.8319	Intermediate Similarity	NPC5103
0.8306	Intermediate Similarity	NPC168879
0.8305	Intermediate Similarity	NPC472257

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 NPC470628 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1592
0.2-0.3	3696
0.3-0.4	2341
0.4-0.5	739
0.5-0.6	309
0.6-0.7	160
0.7-0.8	111
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8205	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD8328	Phase 3
0.7967	Intermediate Similarity	NPD7507	Approved
0.7913	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7492	Approved
0.7863	Intermediate Similarity	NPD6882	Approved
0.7863	Intermediate Similarity	NPD8297	Approved
0.7851	Intermediate Similarity	NPD6059	Approved
0.7851	Intermediate Similarity	NPD6319	Approved
0.7851	Intermediate Similarity	NPD6054	Approved
0.784	Intermediate Similarity	NPD7736	Approved
0.7826	Intermediate Similarity	NPD6686	Approved
0.7826	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6616	Approved
0.7807	Intermediate Similarity	NPD7128	Approved
0.7807	Intermediate Similarity	NPD5739	Approved
0.7807	Intermediate Similarity	NPD6402	Approved
0.7807	Intermediate Similarity	NPD6675	Approved
0.7787	Intermediate Similarity	NPD8516	Approved
0.7787	Intermediate Similarity	NPD8517	Approved
0.7787	Intermediate Similarity	NPD8515	Approved
0.7787	Intermediate Similarity	NPD8513	Phase 3
0.7778	Intermediate Similarity	NPD7319	Approved
0.776	Intermediate Similarity	NPD7078	Approved
0.776	Intermediate Similarity	NPD8293	Discontinued
0.7759	Intermediate Similarity	NPD6372	Approved
0.7759	Intermediate Similarity	NPD6373	Approved
0.775	Intermediate Similarity	NPD6009	Approved
0.7724	Intermediate Similarity	NPD6370	Approved
0.7672	Intermediate Similarity	NPD6881	Approved
0.7672	Intermediate Similarity	NPD7320	Approved
0.7672	Intermediate Similarity	NPD6899	Approved
0.7647	Intermediate Similarity	NPD4632	Approved
0.7642	Intermediate Similarity	NPD6015	Approved
0.7642	Intermediate Similarity	NPD6016	Approved
0.7627	Intermediate Similarity	NPD6649	Approved
0.7627	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6650	Approved
0.7607	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5697	Approved
0.7586	Intermediate Similarity	NPD6412	Phase 2
0.7586	Intermediate Similarity	NPD5701	Approved
0.7581	Intermediate Similarity	NPD5988	Approved
0.7542	Intermediate Similarity	NPD7290	Approved
0.7542	Intermediate Similarity	NPD6883	Approved
0.7542	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD8133	Approved
0.748	Intermediate Similarity	NPD7516	Approved
0.7479	Intermediate Similarity	NPD6617	Approved
0.7479	Intermediate Similarity	NPD6869	Approved
0.7479	Intermediate Similarity	NPD6847	Approved
0.7479	Intermediate Similarity	NPD8130	Phase 1
0.7459	Intermediate Similarity	NPD7115	Discovery
0.7458	Intermediate Similarity	NPD6014	Approved
0.7458	Intermediate Similarity	NPD6012	Approved
0.7458	Intermediate Similarity	NPD6013	Approved
0.7398	Intermediate Similarity	NPD7327	Approved
0.7398	Intermediate Similarity	NPD7328	Approved
0.7395	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7604	Phase 2
0.7373	Intermediate Similarity	NPD6011	Approved
0.7368	Intermediate Similarity	NPD7640	Approved
0.7368	Intermediate Similarity	NPD7639	Approved
0.736	Intermediate Similarity	NPD8033	Approved
0.736	Intermediate Similarity	NPD5983	Phase 2
0.7344	Intermediate Similarity	NPD8074	Phase 3
0.7333	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6033	Approved
0.7281	Intermediate Similarity	NPD7638	Approved
0.7281	Intermediate Similarity	NPD4225	Approved
0.728	Intermediate Similarity	NPD8377	Approved
0.728	Intermediate Similarity	NPD8294	Approved
0.7266	Intermediate Similarity	NPD6336	Discontinued
0.7241	Intermediate Similarity	NPD5211	Phase 2
0.7222	Intermediate Similarity	NPD8379	Approved
0.7222	Intermediate Similarity	NPD8378	Approved
0.7222	Intermediate Similarity	NPD8296	Approved
0.7222	Intermediate Similarity	NPD6921	Approved
0.7222	Intermediate Similarity	NPD8380	Approved
0.7222	Intermediate Similarity	NPD8335	Approved
0.7222	Intermediate Similarity	NPD7503	Approved
0.7203	Intermediate Similarity	NPD6008	Approved
0.7193	Intermediate Similarity	NPD6084	Phase 2
0.7193	Intermediate Similarity	NPD4755	Approved
0.7193	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7119	Intermediate Similarity	NPD5141	Approved
0.7107	Intermediate Similarity	NPD4634	Approved
0.7097	Intermediate Similarity	NPD6274	Approved
0.708	Intermediate Similarity	NPD7748	Approved
0.7069	Intermediate Similarity	NPD5285	Approved
0.7069	Intermediate Similarity	NPD4700	Approved
0.7069	Intermediate Similarity	NPD5286	Approved
0.7069	Intermediate Similarity	NPD4696	Approved
0.7063	Intermediate Similarity	NPD7100	Approved
0.7063	Intermediate Similarity	NPD7101	Approved
0.7054	Intermediate Similarity	NPD7515	Phase 2
0.7054	Intermediate Similarity	NPD6411	Approved
0.7054	Intermediate Similarity	NPD7983	Approved
0.7043	Intermediate Similarity	NPD7902	Approved
0.6984	Remote Similarity	NPD6335	Approved
0.6964	Remote Similarity	NPD6698	Approved
0.6964	Remote Similarity	NPD46	Approved
0.6953	Remote Similarity	NPD6909	Approved
0.6953	Remote Similarity	NPD6908	Approved
0.6949	Remote Similarity	NPD5226	Approved
0.6949	Remote Similarity	NPD5225	Approved
0.6949	Remote Similarity	NPD4633	Approved
0.6949	Remote Similarity	NPD5224	Approved
0.6917	Remote Similarity	NPD4767	Approved
0.6917	Remote Similarity	NPD4768	Approved
0.6905	Remote Similarity	NPD6317	Approved
0.6891	Remote Similarity	NPD5174	Approved
0.6891	Remote Similarity	NPD5175	Approved
0.6875	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5328	Approved
0.6875	Remote Similarity	NPD6101	Approved
0.687	Remote Similarity	NPD5695	Phase 3
0.6864	Remote Similarity	NPD5344	Discontinued
0.6864	Remote Similarity	NPD5223	Approved
0.6855	Remote Similarity	NPD6053	Discontinued
0.685	Remote Similarity	NPD6313	Approved
0.685	Remote Similarity	NPD6314	Approved
0.6847	Remote Similarity	NPD3573	Approved
0.6838	Remote Similarity	NPD5696	Approved
0.6825	Remote Similarity	NPD6868	Approved
0.681	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5222	Approved
0.681	Remote Similarity	NPD4697	Phase 3
0.681	Remote Similarity	NPD5221	Approved
0.6807	Remote Similarity	NPD7632	Discontinued
0.6803	Remote Similarity	NPD4729	Approved
0.6803	Remote Similarity	NPD4730	Approved
0.6786	Remote Similarity	NPD6672	Approved
0.6786	Remote Similarity	NPD5737	Approved
0.6783	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7900	Approved
0.6754	Remote Similarity	NPD6079	Approved
0.6754	Remote Similarity	NPD8034	Phase 2
0.6754	Remote Similarity	NPD8035	Phase 2
0.6752	Remote Similarity	NPD5173	Approved
0.675	Remote Similarity	NPD4754	Approved
0.6741	Remote Similarity	NPD7260	Phase 2
0.6727	Remote Similarity	NPD4786	Approved
0.6721	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6067	Discontinued
0.6697	Remote Similarity	NPD3667	Approved
0.6696	Remote Similarity	NPD7524	Approved
0.6694	Remote Similarity	NPD5251	Approved
0.6694	Remote Similarity	NPD5248	Approved
0.6694	Remote Similarity	NPD5249	Phase 3
0.6694	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5247	Approved
0.6694	Remote Similarity	NPD5250	Approved
0.6692	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7637	Suspended
0.6607	Remote Similarity	NPD3618	Phase 1
0.6607	Remote Similarity	NPD6098	Approved
0.6579	Remote Similarity	NPD6904	Approved
0.6579	Remote Similarity	NPD6080	Approved
0.6579	Remote Similarity	NPD6673	Approved
0.6579	Remote Similarity	NPD4753	Phase 2
0.6569	Remote Similarity	NPD6845	Suspended
0.656	Remote Similarity	NPD6371	Approved
0.6555	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4202	Approved
0.6544	Remote Similarity	NPD5956	Approved
0.6508	Remote Similarity	NPD5216	Approved
0.6508	Remote Similarity	NPD5215	Approved
0.6508	Remote Similarity	NPD5217	Approved
0.65	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6648	Approved
0.6496	Remote Similarity	NPD5282	Discontinued
0.6491	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8415	Approved
0.6466	Remote Similarity	NPD5693	Phase 1
0.646	Remote Similarity	NPD6684	Approved
0.646	Remote Similarity	NPD5330	Approved
0.646	Remote Similarity	NPD7334	Approved
0.646	Remote Similarity	NPD7521	Approved
0.646	Remote Similarity	NPD7146	Approved
0.646	Remote Similarity	NPD6409	Approved
0.6441	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5135	Approved
0.6429	Remote Similarity	NPD5169	Approved
0.6429	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7645	Phase 2
0.6378	Remote Similarity	NPD5127	Approved
0.6364	Remote Similarity	NPD7525	Registered
0.6348	Remote Similarity	NPD6903	Approved
0.6339	Remote Similarity	NPD6695	Phase 3

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