NPASS Compound

Structure

NPC470237 OpenBabel07101719132D 36 36 0 0 1 0 0 0 0 0999 V2000 -10.8654 9.6407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9659 -1.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1583 8.9336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1924 9.1924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9336 10.1583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9676 10.4171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7088 11.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7429 11.6419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0358 10.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0699 11.1936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3628 10.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6216 9.5206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9145 8.8135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1733 7.8475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4662 7.1404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7250 6.1745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0179 5.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1554 2.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2767 4.5015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8966 3.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5696 3.7944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3461 0.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8284 2.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6037 4.0532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 28 2 0 0 0 0 3 29 1 0 0 0 0 4 33 1 0 0 0 0 5 33 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 28 1 0 0 0 0 23 32 1 0 0 0 0 24 25 1 0 0 0 0 24 29 1 0 0 0 0 26 36 1 0 0 0 0 27 30 1 0 0 0 0 27 33 1 0 0 0 0 29 34 2 0 0 0 0 30 28 1 1 0 0 0 30 31 1 0 0 0 0 31 25 1 6 0 0 0 31 33 1 0 0 0 0 32 35 2 0 0 0 0 32 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.42
Volume:	583.956
LogP:	7.813
LogD:	5.652
LogS:	-3.864
# Rotatable Bonds:	23
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.084
Synthetic Accessibility Score:	3.923
Fsp3:	0.758
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.886
MDCK Permeability:	2.241093898192048e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.067
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.396
Plasma Protein Binding (PPB):	99.96752166748047%
Volume Distribution (VD):	2.145
Pgp-substrate:	0.7409906387329102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.295
CYP2C19-inhibitor:	0.239
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.14
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.559
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.839
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	4.854
Half-life (T1/2):	0.82

ADMET: Toxicity

hERG Blockers:	0.518
Human Hepatotoxicity (H-HT):	0.425
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.433
Skin Sensitization:	0.963
Carcinogencity:	0.097
Eye Corrosion:	0.02
Eye Irritation:	0.073
Respiratory Toxicity:	0.883

Download Data

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

Natural Product: NPC470237

Natural Product ID:	NPC470237
*Common Name:**	1Beta,9Alphah-5-Linoleoyloxy-4,5-Secocaryophyllen-4-One
IUPAC Name:	4-[(1R,2S)-3,3-dimethyl-2-(3-oxobutyl)cyclobutyl]pent-4-enyl (9Z,12Z)-octadeca-9,12-dienoate
Synonyms:
Standard InCHIKey:	FNYDLNLBDSWCRW-WCUBTSRTSA-N
Standard InCHI:	InChI=1S/C33H56O3/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23-32(35)36-26-21-22-28(2)30-27-33(4,5)31(30)25-24-29(3)34/h10-11,13-14,30-31H,2,6-9,12,15-27H2,1,3-5H3/b11-10-,14-13-/t30-,31-/m0/s1
SMILES:	CCCCC/C=CC/C=CCCCCCCCC(=O)OCCCC(=C)[C@@H]1CC([C@H]1CCC(=O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1912038
PubChem CID:	57403343
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters [CHEMONTID:0001723] Wax esters [CHEMONTID:0003322] Wax monoesters

*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
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO22238	Inula falconeri	Species	Asteraceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	35500.0	nM	PMID[478485]

☑ 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 NPC470237 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	214
0.1-0.2	1577
0.2-0.3	8189
0.3-0.4	16138
0.4-0.5	8028
0.5-0.6	6560
0.6-0.7	1854
0.7-0.8	132
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8514	High Similarity	NPC474527
0.8514	High Similarity	NPC471726
0.8312	Intermediate Similarity	NPC304795
0.8219	Intermediate Similarity	NPC40327
0.8133	Intermediate Similarity	NPC474419
0.8	Intermediate Similarity	NPC166797
0.7975	Intermediate Similarity	NPC327002
0.7975	Intermediate Similarity	NPC474955
0.7949	Intermediate Similarity	NPC469690
0.7949	Intermediate Similarity	NPC327674
0.7945	Intermediate Similarity	NPC144511
0.7945	Intermediate Similarity	NPC296522
0.7922	Intermediate Similarity	NPC476264
0.7922	Intermediate Similarity	NPC476325
0.7901	Intermediate Similarity	NPC312660
0.7895	Intermediate Similarity	NPC228978
0.7867	Intermediate Similarity	NPC92909
0.7867	Intermediate Similarity	NPC107783
0.7838	Intermediate Similarity	NPC475310
0.7821	Intermediate Similarity	NPC4827
0.7778	Intermediate Similarity	NPC108045
0.7778	Intermediate Similarity	NPC475622
0.7763	Intermediate Similarity	NPC306928
0.7763	Intermediate Similarity	NPC167049
0.7763	Intermediate Similarity	NPC469691
0.7746	Intermediate Similarity	NPC34883
0.7746	Intermediate Similarity	NPC469723
0.7722	Intermediate Similarity	NPC469620
0.7722	Intermediate Similarity	NPC28319
0.7722	Intermediate Similarity	NPC158565
0.7711	Intermediate Similarity	NPC264127
0.7703	Intermediate Similarity	NPC22301
0.7703	Intermediate Similarity	NPC199557
0.7692	Intermediate Similarity	NPC472300
0.7662	Intermediate Similarity	NPC324762
0.7662	Intermediate Similarity	NPC475771
0.7662	Intermediate Similarity	NPC469669
0.7662	Intermediate Similarity	NPC469678
0.7662	Intermediate Similarity	NPC475861
0.7662	Intermediate Similarity	NPC244166
0.7654	Intermediate Similarity	NPC240302
0.7654	Intermediate Similarity	NPC145963
0.7625	Intermediate Similarity	NPC267517
0.7619	Intermediate Similarity	NPC478145
0.7619	Intermediate Similarity	NPC478144
0.7612	Intermediate Similarity	NPC128061
0.7612	Intermediate Similarity	NPC200845
0.7612	Intermediate Similarity	NPC28779
0.7612	Intermediate Similarity	NPC10316
0.7612	Intermediate Similarity	NPC223677
0.76	Intermediate Similarity	NPC472955
0.7595	Intermediate Similarity	NPC471220
0.7595	Intermediate Similarity	NPC35574
0.7595	Intermediate Similarity	NPC321514
0.759	Intermediate Similarity	NPC470223
0.7571	Intermediate Similarity	NPC143857
0.7571	Intermediate Similarity	NPC229252
0.7564	Intermediate Similarity	NPC40353
0.7564	Intermediate Similarity	NPC226242
0.7564	Intermediate Similarity	NPC899
0.7564	Intermediate Similarity	NPC472967
0.7564	Intermediate Similarity	NPC41017
0.7564	Intermediate Similarity	NPC266159
0.7561	Intermediate Similarity	NPC222358
0.7561	Intermediate Similarity	NPC193198
0.7534	Intermediate Similarity	NPC126899
0.7534	Intermediate Similarity	NPC304665
0.7534	Intermediate Similarity	NPC154728
0.7532	Intermediate Similarity	NPC330016
0.7532	Intermediate Similarity	NPC472966
0.7531	Intermediate Similarity	NPC476988
0.7531	Intermediate Similarity	NPC14203
0.7531	Intermediate Similarity	NPC475665
0.7531	Intermediate Similarity	NPC229584
0.7529	Intermediate Similarity	NPC97884
0.7529	Intermediate Similarity	NPC472220
0.75	Intermediate Similarity	NPC325594
0.75	Intermediate Similarity	NPC329943
0.75	Intermediate Similarity	NPC195640
0.75	Intermediate Similarity	NPC82488
0.75	Intermediate Similarity	NPC308545
0.75	Intermediate Similarity	NPC474045
0.75	Intermediate Similarity	NPC91525
0.75	Intermediate Similarity	NPC10005
0.75	Intermediate Similarity	NPC261253
0.75	Intermediate Similarity	NPC9892
0.747	Intermediate Similarity	NPC100391
0.747	Intermediate Similarity	NPC139566
0.7468	Intermediate Similarity	NPC195785
0.7468	Intermediate Similarity	NPC15975
0.7468	Intermediate Similarity	NPC107668
0.7442	Intermediate Similarity	NPC474570
0.7442	Intermediate Similarity	NPC284561
0.7436	Intermediate Similarity	NPC113639
0.7436	Intermediate Similarity	NPC476844
0.7432	Intermediate Similarity	NPC469868
0.7416	Intermediate Similarity	NPC472469
0.7412	Intermediate Similarity	NPC162107
0.7412	Intermediate Similarity	NPC46912
0.7407	Intermediate Similarity	NPC103634
0.7403	Intermediate Similarity	NPC135703
0.7403	Intermediate Similarity	NPC472956
0.7403	Intermediate Similarity	NPC167145
0.7381	Intermediate Similarity	NPC161957
0.7381	Intermediate Similarity	NPC33570
0.7381	Intermediate Similarity	NPC323765
0.7381	Intermediate Similarity	NPC290329
0.7381	Intermediate Similarity	NPC21471
0.7381	Intermediate Similarity	NPC189311
0.7381	Intermediate Similarity	NPC472686
0.7375	Intermediate Similarity	NPC239098
0.7375	Intermediate Similarity	NPC179028
0.7375	Intermediate Similarity	NPC128276
0.7361	Intermediate Similarity	NPC54925
0.7356	Intermediate Similarity	NPC475965
0.7356	Intermediate Similarity	NPC474842
0.7349	Intermediate Similarity	NPC475989
0.7342	Intermediate Similarity	NPC110461
0.7342	Intermediate Similarity	NPC12740
0.7342	Intermediate Similarity	NPC474447
0.7342	Intermediate Similarity	NPC239127
0.7342	Intermediate Similarity	NPC27205
0.7342	Intermediate Similarity	NPC279537
0.7333	Intermediate Similarity	NPC476614
0.7326	Intermediate Similarity	NPC28227
0.7326	Intermediate Similarity	NPC224145
0.7326	Intermediate Similarity	NPC474845
0.7317	Intermediate Similarity	NPC42470
0.7317	Intermediate Similarity	NPC472471
0.7317	Intermediate Similarity	NPC39411
0.7317	Intermediate Similarity	NPC478262
0.7317	Intermediate Similarity	NPC90055
0.7317	Intermediate Similarity	NPC255580
0.7317	Intermediate Similarity	NPC471325
0.7313	Intermediate Similarity	NPC39633
0.7313	Intermediate Similarity	NPC139545
0.7313	Intermediate Similarity	NPC71761
0.7313	Intermediate Similarity	NPC309606
0.7308	Intermediate Similarity	NPC283908
0.7308	Intermediate Similarity	NPC237591
0.7308	Intermediate Similarity	NPC474551
0.7308	Intermediate Similarity	NPC103958
0.7308	Intermediate Similarity	NPC3753
0.7308	Intermediate Similarity	NPC161923
0.7308	Intermediate Similarity	NPC183503
0.7303	Intermediate Similarity	NPC473435
0.7303	Intermediate Similarity	NPC473280
0.7303	Intermediate Similarity	NPC473431
0.7303	Intermediate Similarity	NPC471078
0.7294	Intermediate Similarity	NPC70422
0.7294	Intermediate Similarity	NPC220478
0.7294	Intermediate Similarity	NPC469676
0.7294	Intermediate Similarity	NPC202394
0.7294	Intermediate Similarity	NPC70555
0.7294	Intermediate Similarity	NPC104961
0.7284	Intermediate Similarity	NPC477371
0.7284	Intermediate Similarity	NPC471475
0.7273	Intermediate Similarity	NPC160817
0.7273	Intermediate Similarity	NPC129665
0.7273	Intermediate Similarity	NPC218301
0.7273	Intermediate Similarity	NPC219874
0.7262	Intermediate Similarity	NPC474359
0.7262	Intermediate Similarity	NPC149869
0.7262	Intermediate Similarity	NPC475100
0.725	Intermediate Similarity	NPC122264
0.725	Intermediate Similarity	NPC211279
0.725	Intermediate Similarity	NPC470240
0.725	Intermediate Similarity	NPC57744
0.725	Intermediate Similarity	NPC65603
0.725	Intermediate Similarity	NPC476794
0.725	Intermediate Similarity	NPC165711
0.7246	Intermediate Similarity	NPC252860
0.7241	Intermediate Similarity	NPC475049
0.7241	Intermediate Similarity	NPC474700
0.7241	Intermediate Similarity	NPC50070
0.7237	Intermediate Similarity	NPC469677
0.7237	Intermediate Similarity	NPC477448
0.7237	Intermediate Similarity	NPC477449
0.7229	Intermediate Similarity	NPC35556
0.7229	Intermediate Similarity	NPC200513
0.7229	Intermediate Similarity	NPC296367
0.7229	Intermediate Similarity	NPC100297
0.7222	Intermediate Similarity	NPC125312
0.7222	Intermediate Similarity	NPC174560
0.7215	Intermediate Similarity	NPC193351
0.7215	Intermediate Similarity	NPC138408
0.7215	Intermediate Similarity	NPC192540
0.7215	Intermediate Similarity	NPC279666
0.7215	Intermediate Similarity	NPC155587
0.7215	Intermediate Similarity	NPC255060
0.7215	Intermediate Similarity	NPC226669
0.7209	Intermediate Similarity	NPC167877
0.7195	Intermediate Similarity	NPC474956
0.7195	Intermediate Similarity	NPC47747
0.7195	Intermediate Similarity	NPC195424
0.7195	Intermediate Similarity	NPC104545
0.7195	Intermediate Similarity	NPC472470
0.7195	Intermediate Similarity	NPC477057
0.7191	Intermediate Similarity	NPC169343
0.7191	Intermediate Similarity	NPC471571

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 NPC470237 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	2225
0.2-0.3	3997
0.3-0.4	1844
0.4-0.5	556
0.5-0.6	245
0.6-0.7	72
0.7-0.8	1
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
0.7895	Intermediate Similarity	NPD8039	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7375	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5737	Approved
0.7326	Intermediate Similarity	NPD6903	Approved
0.7326	Intermediate Similarity	NPD6672	Approved
0.7326	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6435	Approved
0.7229	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1694	Approved
0.7111	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7900	Approved
0.7111	Intermediate Similarity	NPD7748	Approved
0.7108	Intermediate Similarity	NPD5369	Approved
0.7093	Intermediate Similarity	NPD6098	Approved
0.7079	Intermediate Similarity	NPD6411	Approved
0.7015	Intermediate Similarity	NPD29	Approved
0.7015	Intermediate Similarity	NPD28	Approved
0.7011	Intermediate Similarity	NPD3573	Approved
0.7	Intermediate Similarity	NPD6399	Phase 3
0.6988	Remote Similarity	NPD5368	Approved
0.6941	Remote Similarity	NPD5362	Discontinued
0.6941	Remote Similarity	NPD7154	Phase 3
0.6882	Remote Similarity	NPD7902	Approved
0.6854	Remote Similarity	NPD6673	Approved
0.6854	Remote Similarity	NPD6904	Approved
0.6854	Remote Similarity	NPD6080	Approved
0.6854	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6101	Approved
0.6824	Remote Similarity	NPD5209	Approved
0.6824	Remote Similarity	NPD4269	Approved
0.6824	Remote Similarity	NPD4270	Approved
0.6778	Remote Similarity	NPD5207	Approved
0.6778	Remote Similarity	NPD5785	Approved
0.6742	Remote Similarity	NPD5208	Approved
0.6714	Remote Similarity	NPD4266	Approved
0.6714	Remote Similarity	NPD3196	Approved
0.6714	Remote Similarity	NPD3194	Approved
0.6714	Remote Similarity	NPD3195	Phase 2
0.6706	Remote Similarity	NPD857	Phase 3
0.6705	Remote Similarity	NPD5786	Approved
0.6703	Remote Similarity	NPD5694	Approved
0.6703	Remote Similarity	NPD7515	Phase 2
0.6703	Remote Similarity	NPD6050	Approved
0.6702	Remote Similarity	NPD6083	Phase 2
0.6702	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4786	Approved
0.663	Remote Similarity	NPD5778	Approved
0.663	Remote Similarity	NPD5779	Approved
0.6628	Remote Similarity	NPD3667	Approved
0.6623	Remote Similarity	NPD7331	Phase 2
0.6593	Remote Similarity	NPD5692	Phase 3
0.6591	Remote Similarity	NPD5363	Approved
0.6588	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4252	Approved
0.6579	Remote Similarity	NPD3197	Phase 1
0.6579	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3172	Approved
0.6567	Remote Similarity	NPD5343	Approved
0.6522	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD5693	Phase 1
0.6494	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7341	Phase 2
0.6477	Remote Similarity	NPD3665	Phase 1
0.6477	Remote Similarity	NPD3668	Phase 3
0.6477	Remote Similarity	NPD3133	Approved
0.6477	Remote Similarity	NPD3666	Approved
0.6458	Remote Similarity	NPD5696	Approved
0.6421	Remote Similarity	NPD7732	Phase 3
0.641	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4695	Discontinued
0.6395	Remote Similarity	NPD4820	Approved
0.6395	Remote Similarity	NPD4819	Approved
0.6395	Remote Similarity	NPD4822	Approved
0.6395	Remote Similarity	NPD4821	Approved
0.6383	Remote Similarity	NPD6001	Approved
0.6383	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD5331	Approved
0.6364	Remote Similarity	NPD5332	Approved
0.6353	Remote Similarity	NPD4271	Approved
0.6353	Remote Similarity	NPD4268	Approved
0.6351	Remote Similarity	NPD287	Approved
0.6344	Remote Similarity	NPD6079	Approved
0.6344	Remote Similarity	NPD8035	Phase 2
0.6344	Remote Similarity	NPD5284	Approved
0.6344	Remote Similarity	NPD5281	Approved
0.6344	Remote Similarity	NPD8034	Phase 2
0.6333	Remote Similarity	NPD3618	Phase 1
0.6333	Remote Similarity	NPD6422	Discontinued
0.6333	Remote Similarity	NPD5279	Phase 3
0.6322	Remote Similarity	NPD4790	Discontinued
0.6304	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5328	Approved
0.6304	Remote Similarity	NPD1695	Approved
0.6292	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6881	Approved
0.6275	Remote Similarity	NPD6899	Approved
0.6269	Remote Similarity	NPD3174	Discontinued
0.625	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4221	Approved
0.625	Remote Similarity	NPD4223	Phase 3
0.625	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD8130	Phase 1
0.6238	Remote Similarity	NPD6675	Approved
0.6238	Remote Similarity	NPD6402	Approved
0.6238	Remote Similarity	NPD5739	Approved
0.6238	Remote Similarity	NPD7128	Approved
0.6237	Remote Similarity	NPD3673	Approved
0.6237	Remote Similarity	NPD6698	Approved
0.6237	Remote Similarity	NPD3672	Approved
0.6237	Remote Similarity	NPD46	Approved
0.6222	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5329	Approved
0.6222	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5777	Approved
0.6207	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8297	Approved
0.6176	Remote Similarity	NPD5697	Approved
0.6173	Remote Similarity	NPD4137	Phase 3
0.617	Remote Similarity	NPD7637	Suspended
0.6163	Remote Similarity	NPD3732	Approved
0.6154	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD4519	Discontinued
0.6154	Remote Similarity	NPD4623	Approved
0.6154	Remote Similarity	NPD5690	Phase 2
0.6154	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD6883	Approved
0.6146	Remote Similarity	NPD5654	Approved
0.6129	Remote Similarity	NPD6051	Approved
0.6129	Remote Similarity	NPD4753	Phase 2
0.6122	Remote Similarity	NPD7638	Approved
0.6119	Remote Similarity	NPD6097	Approved
0.6119	Remote Similarity	NPD6096	Approved
0.6117	Remote Similarity	NPD6011	Approved
0.6117	Remote Similarity	NPD7320	Approved
0.6111	Remote Similarity	NPD4197	Approved
0.6098	Remote Similarity	NPD4691	Approved
0.6098	Remote Similarity	NPD4747	Approved
0.6095	Remote Similarity	NPD6650	Approved
0.6095	Remote Similarity	NPD6617	Approved
0.6095	Remote Similarity	NPD6847	Approved
0.6095	Remote Similarity	NPD6869	Approved
0.6095	Remote Similarity	NPD6649	Approved
0.6087	Remote Similarity	NPD4250	Approved
0.6087	Remote Similarity	NPD4251	Approved
0.6078	Remote Similarity	NPD6008	Approved
0.6071	Remote Similarity	NPD4058	Approved
0.6071	Remote Similarity	NPD5733	Approved
0.6071	Remote Similarity	NPD4687	Approved
0.6064	Remote Similarity	NPD7838	Discovery
0.6061	Remote Similarity	NPD7639	Approved
0.6061	Remote Similarity	NPD7640	Approved
0.6058	Remote Similarity	NPD6372	Approved
0.6058	Remote Similarity	NPD6013	Approved
0.6058	Remote Similarity	NPD6014	Approved
0.6058	Remote Similarity	NPD6373	Approved
0.6058	Remote Similarity	NPD6012	Approved
0.6056	Remote Similarity	NPD6927	Phase 3
0.6049	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6052	Approved
0.6038	Remote Similarity	NPD6882	Approved
0.6027	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD5276	Approved
0.6022	Remote Similarity	NPD4518	Approved
0.602	Remote Similarity	NPD5959	Approved
0.6019	Remote Similarity	NPD6614	Approved
0.6019	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD3173	Approved
0.6	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD6371	Approved
0.5981	Remote Similarity	NPD7094	Approved
0.5981	Remote Similarity	NPD6858	Approved
0.5979	Remote Similarity	NPD5210	Approved
0.5979	Remote Similarity	NPD4629	Approved
0.5978	Remote Similarity	NPD4249	Approved
0.5978	Remote Similarity	NPD4689	Approved
0.5978	Remote Similarity	NPD4694	Approved
0.5978	Remote Similarity	NPD5280	Approved
0.5978	Remote Similarity	NPD4693	Phase 3
0.5978	Remote Similarity	NPD5205	Approved
0.5978	Remote Similarity	NPD4690	Approved
0.5978	Remote Similarity	NPD4138	Approved
0.5978	Remote Similarity	NPD4688	Approved
0.5977	Remote Similarity	NPD3617	Approved
0.5974	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6686	Approved
0.5957	Remote Similarity	NPD5370	Suspended
0.5943	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4202	Approved
0.5918	Remote Similarity	NPD7614	Phase 1

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