NPASS Compound

Structure

NPC179128 OpenBabel07101719252D 38 41 0 0 1 0 0 0 0 0999 V2000 -2.4694 -6.3909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5170 -6.3909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2078 -3.0093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6583 0.3561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0289 -3.8547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3224 1.5518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9813 -5.5455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5554 -1.0569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8646 -1.0569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5554 -0.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8646 -0.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5170 -4.7001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0051 -3.8547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3624 -1.5450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0192 -1.5450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1738 -3.0093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0051 -5.5455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3624 -2.5212 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9600 -0.5723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7100 -1.5450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7100 0.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0192 -2.5212 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1738 -1.0569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3284 -2.5212 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5170 -1.0569 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7100 -2.5212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9708 -0.1020 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3971 -0.8918 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5170 -3.0093 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3284 -1.5450 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9148 -0.7752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7100 1.3836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5170 -0.0807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5554 -3.0093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6240 0.6234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3068 -1.2977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8646 -3.0093 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 7 2 0 0 0 0 2 17 2 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 6 35 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 20 2 0 0 0 0 9 11 2 0 0 0 0 9 20 1 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 29 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 15 23 2 0 0 0 0 16 22 1 0 0 0 0 16 24 1 0 0 0 0 18 29 1 6 0 0 0 19 31 2 0 0 0 0 19 36 1 0 0 0 0 20 26 1 0 0 0 0 21 32 1 0 0 0 0 22 37 1 1 0 0 0 23 27 1 0 0 0 0 24 29 1 1 0 0 0 24 30 1 0 0 0 0 25 30 1 6 0 0 0 25 33 1 0 0 0 0 26 34 2 0 0 0 0 26 37 1 0 0 0 0 27 35 1 6 0 0 0 27 38 1 0 0 0 0 28 30 1 6 0 0 0 28 36 1 0 0 0 0 28 38 1 0 0 0 0 29 5 1 1 0 0 0 30 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.26
Volume:	542.44
LogP:	3.989
LogD:	3.574
LogS:	-4.265
# Rotatable Bonds:	10
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.286
Synthetic Accessibility Score:	5.592
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.802
MDCK Permeability:	2.2266158339334652e-05
Pgp-inhibitor:	0.293
Pgp-substrate:	0.781
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.71

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.492
Plasma Protein Binding (PPB):	91.0468978881836%
Volume Distribution (VD):	1.13
Pgp-substrate:	10.076972007751465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.15
CYP2C9-inhibitor:	0.43
CYP2C9-substrate:	0.194
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.458
CYP3A4-inhibitor:	0.662
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	6.369
Half-life (T1/2):	0.349

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.196
Rat Oral Acute Toxicity:	0.949
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.818
Carcinogencity:	0.881
Eye Corrosion:	0.005
Eye Irritation:	0.026
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC179128

Natural Product ID:	NPC179128
*Common Name:**	Intrapetacin A
IUPAC Name:	[(1S,3S,5S,6aS,7R,8R,10S,10aS)-1-acetyloxy-10-hydroxy-3-methoxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] 4-hydroxybenzoate
Synonyms:
Standard InCHIKey:	NXJIENULLHZFNA-NTICDAHTSA-N
Standard InCHI:	InChI=1S/C30H38O8/c1-7-17(2)12-13-29(5)18(3)14-25(33)30-23(27(35-6)38-28(30)36-19(4)31)15-22(16-24(29)30)37-26(34)20-8-10-21(32)11-9-20/h7-11,15,18,22,24-25,27-28,32-33H,1-2,12-14,16H2,3-6H3/t18-,22-,24+,25+,27+,28-,29-,30-/m1/s1
SMILES:	CO[C@H]1O[C@H]([C@@]23C1=C[C@H](C[C@H]3[C@]([C@@H](C[C@@H]2O)C)(C)CCC(=C)C=C)OC(=O)c1ccc(cc1)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516046
PubChem CID:	44584771
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO17756	Licania intrapetiolaris	Species	Chrysobalanaceae	Eukaryota	roots	n.a.	n.a.	PMID[11325234]
NPO17756	Licania intrapetiolaris	Species	Chrysobalanaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	2.0	ug.mL-1	PMID[496734]

☑ 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 NPC179128 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	312
0.1-0.2	1156
0.2-0.3	2460
0.3-0.4	4338
0.4-0.5	9058
0.5-0.6	9887
0.6-0.7	9250
0.7-0.8	5977
0.8-0.85	225
0.85-0.9	24
0.9-0.95	3
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC116292
1.0	High Similarity	NPC267469
1.0	High Similarity	NPC87630
0.986	High Similarity	NPC162569
0.986	High Similarity	NPC35160
0.9718	High Similarity	NPC208293
0.9091	High Similarity	NPC477627
0.9048	High Similarity	NPC320734
0.8981	High Similarity	NPC469458
0.8981	High Similarity	NPC88176
0.8981	High Similarity	NPC469459
0.8981	High Similarity	NPC469396
0.8981	High Similarity	NPC469419
0.8981	High Similarity	NPC149002
0.8968	High Similarity	NPC293568
0.8968	High Similarity	NPC117943
0.8926	High Similarity	NPC477483
0.8926	High Similarity	NPC325032
0.8859	High Similarity	NPC470330
0.8854	High Similarity	NPC100420
0.8811	High Similarity	NPC473216
0.8811	High Similarity	NPC473399
0.8808	High Similarity	NPC247219
0.8797	High Similarity	NPC265600
0.8758	High Similarity	NPC477617
0.8758	High Similarity	NPC148185
0.8742	High Similarity	NPC279442
0.8716	High Similarity	NPC204644
0.8716	High Similarity	NPC478250
0.8684	High Similarity	NPC327962
0.8649	High Similarity	NPC477595
0.8636	High Similarity	NPC257847
0.8616	High Similarity	NPC120012
0.8553	High Similarity	NPC66991
0.8545	High Similarity	NPC260300
0.8545	High Similarity	NPC80360
0.8545	High Similarity	NPC469418
0.8537	High Similarity	NPC469438
0.8535	High Similarity	NPC104275
0.8535	High Similarity	NPC4747
0.8528	High Similarity	NPC13989
0.8526	High Similarity	NPC472807
0.8506	High Similarity	NPC158546
0.8506	High Similarity	NPC140133
0.8506	High Similarity	NPC289021
0.85	High Similarity	NPC161151
0.8497	Intermediate Similarity	NPC161955
0.8494	Intermediate Similarity	NPC195114
0.8487	Intermediate Similarity	NPC286038
0.8456	Intermediate Similarity	NPC172311
0.8443	Intermediate Similarity	NPC188217
0.8435	Intermediate Similarity	NPC471345
0.8431	Intermediate Similarity	NPC469448
0.8428	Intermediate Similarity	NPC130489
0.8428	Intermediate Similarity	NPC208676
0.8425	Intermediate Similarity	NPC194970
0.8424	Intermediate Similarity	NPC469354
0.8421	Intermediate Similarity	NPC258856
0.8411	Intermediate Similarity	NPC77922
0.8411	Intermediate Similarity	NPC296659
0.8411	Intermediate Similarity	NPC202391
0.8411	Intermediate Similarity	NPC473281
0.8411	Intermediate Similarity	NPC100242
0.8408	Intermediate Similarity	NPC172920
0.8408	Intermediate Similarity	NPC156624
0.8387	Intermediate Similarity	NPC133430
0.8387	Intermediate Similarity	NPC469477
0.838	Intermediate Similarity	NPC110211
0.838	Intermediate Similarity	NPC204579
0.8378	Intermediate Similarity	NPC22676
0.8378	Intermediate Similarity	NPC216940
0.8378	Intermediate Similarity	NPC475482
0.8378	Intermediate Similarity	NPC477592
0.8378	Intermediate Similarity	NPC198621
0.8377	Intermediate Similarity	NPC473719
0.8375	Intermediate Similarity	NPC266365
0.8373	Intermediate Similarity	NPC469397
0.8367	Intermediate Similarity	NPC472374
0.8367	Intermediate Similarity	NPC472372
0.8365	Intermediate Similarity	NPC314795
0.8356	Intermediate Similarity	NPC114116
0.8354	Intermediate Similarity	NPC148323
0.8354	Intermediate Similarity	NPC283480
0.8344	Intermediate Similarity	NPC469417
0.8333	Intermediate Similarity	NPC117899
0.8333	Intermediate Similarity	NPC48671
0.8333	Intermediate Similarity	NPC478235
0.8323	Intermediate Similarity	NPC145847
0.8323	Intermediate Similarity	NPC97637
0.8323	Intermediate Similarity	NPC187934
0.8322	Intermediate Similarity	NPC472547
0.8322	Intermediate Similarity	NPC90614
0.8322	Intermediate Similarity	NPC230331
0.8311	Intermediate Similarity	NPC249817
0.831	Intermediate Similarity	NPC470816
0.8302	Intermediate Similarity	NPC226759
0.8302	Intermediate Similarity	NPC187205
0.8301	Intermediate Similarity	NPC75295
0.8301	Intermediate Similarity	NPC473867
0.8299	Intermediate Similarity	NPC477893
0.8291	Intermediate Similarity	NPC469399
0.8291	Intermediate Similarity	NPC82190
0.8291	Intermediate Similarity	NPC192219
0.8291	Intermediate Similarity	NPC174599
0.828	Intermediate Similarity	NPC229354
0.8278	Intermediate Similarity	NPC477894
0.8272	Intermediate Similarity	NPC109990
0.8272	Intermediate Similarity	NPC471861
0.8269	Intermediate Similarity	NPC472658
0.8269	Intermediate Similarity	NPC472657
0.8269	Intermediate Similarity	NPC474620
0.8269	Intermediate Similarity	NPC37642
0.8267	Intermediate Similarity	NPC118080
0.8267	Intermediate Similarity	NPC87448
0.8267	Intermediate Similarity	NPC291599
0.8267	Intermediate Similarity	NPC27377
0.8267	Intermediate Similarity	NPC472576
0.8267	Intermediate Similarity	NPC41481
0.8267	Intermediate Similarity	NPC97947
0.8264	Intermediate Similarity	NPC473744
0.8264	Intermediate Similarity	NPC193203
0.8263	Intermediate Similarity	NPC475054
0.8258	Intermediate Similarity	NPC478236
0.8258	Intermediate Similarity	NPC469415
0.8258	Intermediate Similarity	NPC478234
0.8258	Intermediate Similarity	NPC96599
0.8258	Intermediate Similarity	NPC17600
0.8255	Intermediate Similarity	NPC119542
0.8253	Intermediate Similarity	NPC195972
0.8253	Intermediate Similarity	NPC316539
0.825	Intermediate Similarity	NPC53139
0.825	Intermediate Similarity	NPC68619
0.8247	Intermediate Similarity	NPC473149
0.8243	Intermediate Similarity	NPC173569
0.8243	Intermediate Similarity	NPC477874
0.8239	Intermediate Similarity	NPC474532
0.8235	Intermediate Similarity	NPC469513
0.8231	Intermediate Similarity	NPC48929
0.8228	Intermediate Similarity	NPC209393
0.8228	Intermediate Similarity	NPC205172
0.8225	Intermediate Similarity	NPC102367
0.8219	Intermediate Similarity	NPC18798
0.8217	Intermediate Similarity	NPC469422
0.8217	Intermediate Similarity	NPC34066
0.8217	Intermediate Similarity	NPC11892
0.8217	Intermediate Similarity	NPC5115
0.8217	Intermediate Similarity	NPC469456
0.8212	Intermediate Similarity	NPC472801
0.8207	Intermediate Similarity	NPC147561
0.8205	Intermediate Similarity	NPC117346
0.8205	Intermediate Similarity	NPC52931
0.8205	Intermediate Similarity	NPC212257
0.8205	Intermediate Similarity	NPC88886
0.8205	Intermediate Similarity	NPC104172
0.8205	Intermediate Similarity	NPC240592
0.8205	Intermediate Similarity	NPC12006
0.8205	Intermediate Similarity	NPC35097
0.82	Intermediate Similarity	NPC100913
0.82	Intermediate Similarity	NPC477593
0.82	Intermediate Similarity	NPC171207
0.82	Intermediate Similarity	NPC97667
0.82	Intermediate Similarity	NPC275592
0.8199	Intermediate Similarity	NPC329960
0.8199	Intermediate Similarity	NPC295408
0.8199	Intermediate Similarity	NPC150893
0.8194	Intermediate Similarity	NPC120728
0.8194	Intermediate Similarity	NPC303429
0.8194	Intermediate Similarity	NPC5568
0.8194	Intermediate Similarity	NPC81835
0.8194	Intermediate Similarity	NPC471734
0.8194	Intermediate Similarity	NPC222102
0.8188	Intermediate Similarity	NPC39549
0.8188	Intermediate Similarity	NPC154485
0.8188	Intermediate Similarity	NPC471872
0.8187	Intermediate Similarity	NPC208651
0.8187	Intermediate Similarity	NPC257309
0.8187	Intermediate Similarity	NPC206641
0.8182	Intermediate Similarity	NPC474268
0.8182	Intermediate Similarity	NPC475539
0.8182	Intermediate Similarity	NPC275576
0.8182	Intermediate Similarity	NPC291153
0.8182	Intermediate Similarity	NPC119773
0.8182	Intermediate Similarity	NPC137416
0.8182	Intermediate Similarity	NPC476017
0.8182	Intermediate Similarity	NPC97188
0.8182	Intermediate Similarity	NPC473147
0.8182	Intermediate Similarity	NPC143246
0.8176	Intermediate Similarity	NPC477896
0.8176	Intermediate Similarity	NPC477594
0.8176	Intermediate Similarity	NPC41880
0.8176	Intermediate Similarity	NPC159692
0.8176	Intermediate Similarity	NPC472835
0.817	Intermediate Similarity	NPC194938
0.8169	Intermediate Similarity	NPC470815
0.8158	Intermediate Similarity	NPC91703
0.8158	Intermediate Similarity	NPC163087
0.8155	Intermediate Similarity	NPC11062
0.8155	Intermediate Similarity	NPC475613
0.8153	Intermediate Similarity	NPC77310
0.8153	Intermediate Similarity	NPC140151

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 NPC179128 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	766
0.2-0.3	1448
0.3-0.4	2510
0.4-0.5	2284
0.5-0.6	1340
0.6-0.7	437
0.7-0.8	107
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
0.8039	Intermediate Similarity	NPD4628	Phase 3
0.7975	Intermediate Similarity	NPD7458	Discontinued
0.7905	Intermediate Similarity	NPD3764	Approved
0.7904	Intermediate Similarity	NPD7799	Discontinued
0.7826	Intermediate Similarity	NPD37	Approved
0.7821	Intermediate Similarity	NPD7236	Approved
0.7791	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD4967	Phase 2
0.7746	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD9545	Approved
0.7744	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7266	Discontinued
0.7719	Intermediate Similarity	NPD7685	Pre-registration
0.7719	Intermediate Similarity	NPD6559	Discontinued
0.7718	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD8434	Phase 2
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7692	Intermediate Similarity	NPD3818	Discontinued
0.7692	Intermediate Similarity	NPD8166	Discontinued
0.7692	Intermediate Similarity	NPD7228	Approved
0.7688	Intermediate Similarity	NPD7239	Suspended
0.7673	Intermediate Similarity	NPD6273	Approved
0.7669	Intermediate Similarity	NPD7819	Suspended
0.7658	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD8312	Approved
0.763	Intermediate Similarity	NPD8313	Approved
0.7628	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6663	Approved
0.761	Intermediate Similarity	NPD2533	Approved
0.761	Intermediate Similarity	NPD2532	Approved
0.761	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2534	Approved
0.7584	Intermediate Similarity	NPD5736	Approved
0.758	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7075	Discontinued
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7468	Intermediate Similarity	NPD3750	Approved
0.7468	Intermediate Similarity	NPD7003	Approved
0.7455	Intermediate Similarity	NPD8455	Phase 2
0.7455	Intermediate Similarity	NPD5760	Phase 2
0.7455	Intermediate Similarity	NPD5761	Phase 2
0.7452	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5844	Phase 1
0.7442	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7054	Approved
0.7436	Intermediate Similarity	NPD2935	Discontinued
0.7427	Intermediate Similarity	NPD7473	Discontinued
0.7421	Intermediate Similarity	NPD6190	Approved
0.7416	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD230	Phase 1
0.7401	Intermediate Similarity	NPD8150	Discontinued
0.74	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7472	Approved
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7386	Intermediate Similarity	NPD8407	Phase 2
0.7365	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6232	Discontinued
0.7349	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7411	Suspended
0.7317	Intermediate Similarity	NPD3226	Approved
0.7317	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD8368	Discontinued
0.7314	Intermediate Similarity	NPD7240	Approved
0.7314	Intermediate Similarity	NPD7251	Discontinued
0.7289	Intermediate Similarity	NPD6801	Discontinued
0.7284	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2932	Approved
0.7273	Intermediate Similarity	NPD8320	Phase 1
0.7273	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD8319	Approved
0.7262	Intermediate Similarity	NPD7058	Phase 2
0.7262	Intermediate Similarity	NPD7768	Phase 2
0.7262	Intermediate Similarity	NPD7057	Phase 3
0.7261	Intermediate Similarity	NPD1510	Phase 2
0.7257	Intermediate Similarity	NPD6797	Phase 2
0.725	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1549	Phase 2
0.7219	Intermediate Similarity	NPD7435	Discontinued
0.7216	Intermediate Similarity	NPD6764	Approved
0.7216	Intermediate Similarity	NPD6765	Approved
0.7215	Intermediate Similarity	NPD5408	Approved
0.7215	Intermediate Similarity	NPD6099	Approved
0.7215	Intermediate Similarity	NPD5404	Approved
0.7215	Intermediate Similarity	NPD5405	Approved
0.7215	Intermediate Similarity	NPD6100	Approved
0.7215	Intermediate Similarity	NPD5406	Approved
0.7209	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6959	Discontinued
0.7188	Intermediate Similarity	NPD2800	Approved
0.717	Intermediate Similarity	NPD6004	Phase 3
0.717	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6002	Phase 3
0.717	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6005	Phase 3
0.7169	Intermediate Similarity	NPD7028	Phase 2
0.7168	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3019	Approved
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD3748	Approved
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.7134	Intermediate Similarity	NPD6651	Approved
0.7134	Intermediate Similarity	NPD1607	Approved
0.7133	Intermediate Similarity	NPD1608	Approved
0.7133	Intermediate Similarity	NPD3972	Approved
0.7118	Intermediate Similarity	NPD3749	Approved
0.7115	Intermediate Similarity	NPD1240	Approved
0.7115	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4140	Approved
0.7107	Intermediate Similarity	NPD2796	Approved
0.7083	Intermediate Similarity	NPD1934	Approved
0.7073	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD2346	Discontinued
0.7063	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6778	Approved
0.7059	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD6781	Approved
0.7059	Intermediate Similarity	NPD6776	Approved
0.7059	Intermediate Similarity	NPD6780	Approved
0.7059	Intermediate Similarity	NPD6782	Approved
0.7059	Intermediate Similarity	NPD6777	Approved
0.7059	Intermediate Similarity	NPD2798	Approved
0.7056	Intermediate Similarity	NPD6785	Approved
0.7056	Intermediate Similarity	NPD6784	Approved
0.7053	Intermediate Similarity	NPD7999	Approved
0.7052	Intermediate Similarity	NPD5710	Approved
0.7052	Intermediate Similarity	NPD7229	Phase 3
0.7052	Intermediate Similarity	NPD5711	Approved
0.7051	Intermediate Similarity	NPD8032	Phase 2
0.7047	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1283	Approved
0.7037	Intermediate Similarity	NPD7696	Phase 3
0.7037	Intermediate Similarity	NPD7698	Approved
0.7037	Intermediate Similarity	NPD7697	Approved
0.7035	Intermediate Similarity	NPD5494	Approved
0.7033	Intermediate Similarity	NPD8360	Approved
0.7033	Intermediate Similarity	NPD8361	Approved
0.7032	Intermediate Similarity	NPD7008	Discontinued
0.7031	Intermediate Similarity	NPD8151	Discontinued
0.7026	Intermediate Similarity	NPD7930	Approved
0.7017	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6799	Approved
0.7012	Intermediate Similarity	NPD7390	Discontinued
0.7011	Intermediate Similarity	NPD6213	Phase 3
0.7011	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6212	Phase 3
0.7007	Intermediate Similarity	NPD9493	Approved
0.7006	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD7870	Phase 2
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD3817	Phase 2
0.6995	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7874	Approved
0.6993	Remote Similarity	NPD1470	Approved
0.6993	Remote Similarity	NPD3094	Phase 2
0.6993	Remote Similarity	NPD2797	Approved
0.6987	Remote Similarity	NPD3268	Approved
0.6981	Remote Similarity	NPD7097	Phase 1
0.698	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6166	Phase 2
0.6971	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6832	Phase 2
0.6966	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7783	Phase 2
0.6959	Remote Similarity	NPD3882	Suspended
0.6959	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2344	Approved
0.6954	Remote Similarity	NPD1201	Approved
0.6946	Remote Similarity	NPD1653	Approved
0.6944	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1465	Phase 2
0.694	Remote Similarity	NPD8435	Approved
0.6937	Remote Similarity	NPD4308	Phase 3
0.6933	Remote Similarity	NPD5125	Phase 3
0.6933	Remote Similarity	NPD5126	Approved
0.6933	Remote Similarity	NPD4109	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