NPASS Compound

Structure

NPC98009 OpenBabel07101718182D 30 32 0 0 1 0 0 0 0 0999 V2000 -3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5622 -2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5622 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 3.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6962 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 3.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5622 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4282 -1.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 4.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 -2.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 3.8660 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 28 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 1 1 6 0 0 0 12 21 1 0 0 0 0 12 29 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 1 0 0 0 15 22 1 6 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 28 1 0 0 0 0 18 22 1 1 0 0 0 18 30 1 0 0 0 0 19 24 2 0 0 0 0 19 30 1 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 21 26 2 0 0 0 0 22 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.15
Volume:	412.629
LogP:	2.058
LogD:	0.609
LogS:	-2.756
# Rotatable Bonds:	9
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	4.524
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.676
MDCK Permeability:	1.7163723896373995e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.906
Plasma Protein Binding (PPB):	88.93165588378906%
Volume Distribution (VD):	0.402
Pgp-substrate:	13.233789443969727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.36
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.222
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	11.45
Half-life (T1/2):	0.931

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.215
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.289
Carcinogencity:	0.443
Eye Corrosion:	0.274
Eye Irritation:	0.235
Respiratory Toxicity:	0.293

Download Data

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

Natural Product: NPC98009

Natural Product ID:	NPC98009
*Common Name:**	Brevipolide J
IUPAC Name:	[(2S)-1-[(1S,2S)-2-[(S)-hydroxy-[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate
Synonyms:	Brevipolide J
Standard InCHIKey:	BDIGJZNTLJAZGG-YVGDPVPUSA-N
Standard InCHI:	InChI=1S/C22H24O8/c1-12(29-20(25)9-7-13-6-8-17(28-2)16(23)10-13)21(26)14-11-15(14)22(27)18-4-3-5-19(24)30-18/h3,5-10,12,14-15,18,22-23,27H,4,11H2,1-2H3/b9-7+/t12-,14-,15-,18+,22-/m0/s1
SMILES:	C[C@@H](C(=O)[C@H]1C[C@@H]1[C@@H]([C@H]1CC=CC(=O)O1)O)OC(=O)/C=C/c1ccc(c(c1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337107
PubChem CID:	71521916
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	Whole Plant	Tawangmangu village, Karanganyar, Central Java, Indonesia	2003-FEB	PMID[19422206]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19422206]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23282042]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28099005]
NPO25696	Hyptis brevipes	Species	Lamiaceae	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
ED50	5
IC50	1

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[449591]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[449591]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[449591]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[449591]
NPT65	Cell Line	HepG2	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[449591]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.2	ug.mL-1	PMID[449591]

☑ 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 NPC98009 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	338
0.1-0.2	1336
0.2-0.3	3446
0.3-0.4	7639
0.4-0.5	10116
0.5-0.6	5295
0.6-0.7	8702
0.7-0.8	5544
0.8-0.85	251
0.85-0.9	23
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9571	High Similarity	NPC477278
0.9571	High Similarity	NPC477277
0.95	High Similarity	NPC477279
0.9214	High Similarity	NPC71638
0.9214	High Similarity	NPC64230
0.9155	High Similarity	NPC289690
0.9155	High Similarity	NPC288452
0.9155	High Similarity	NPC322021
0.9041	High Similarity	NPC98356
0.9	High Similarity	NPC477281
0.9	High Similarity	NPC477280
0.9	High Similarity	NPC19719
0.8951	High Similarity	NPC284409
0.8929	High Similarity	NPC323379
0.8929	High Similarity	NPC327204
0.8874	High Similarity	NPC327225
0.8874	High Similarity	NPC44730
0.8851	High Similarity	NPC221383
0.8851	High Similarity	NPC143892
0.8851	High Similarity	NPC299090
0.8851	High Similarity	NPC283081
0.8844	High Similarity	NPC469683
0.8792	High Similarity	NPC1580
0.8792	High Similarity	NPC472969
0.8776	High Similarity	NPC160378
0.8776	High Similarity	NPC469615
0.8741	High Similarity	NPC139519
0.8732	High Similarity	NPC155209
0.8732	High Similarity	NPC168799
0.8732	High Similarity	NPC129889
0.8732	High Similarity	NPC307006
0.8716	High Similarity	NPC258671
0.8716	High Similarity	NPC53884
0.8701	High Similarity	NPC470896
0.8701	High Similarity	NPC473275
0.8693	High Similarity	NPC477299
0.869	High Similarity	NPC325625
0.8684	High Similarity	NPC246566
0.8684	High Similarity	NPC163883
0.8684	High Similarity	NPC95498
0.8684	High Similarity	NPC93498
0.8681	High Similarity	NPC90431
0.8671	High Similarity	NPC471110
0.8662	High Similarity	NPC25581
0.8662	High Similarity	NPC61
0.8662	High Similarity	NPC18074
0.8662	High Similarity	NPC239302
0.8662	High Similarity	NPC5419
0.8652	High Similarity	NPC172673
0.8649	High Similarity	NPC239608
0.8649	High Similarity	NPC46161
0.8649	High Similarity	NPC473090
0.8649	High Similarity	NPC304956
0.8639	High Similarity	NPC253481
0.8639	High Similarity	NPC253722
0.8639	High Similarity	NPC31751
0.863	High Similarity	NPC26241
0.863	High Similarity	NPC303683
0.863	High Similarity	NPC295492
0.863	High Similarity	NPC476820
0.863	High Similarity	NPC147379
0.863	High Similarity	NPC205751
0.863	High Similarity	NPC476819
0.863	High Similarity	NPC274891
0.863	High Similarity	NPC474875
0.863	High Similarity	NPC474784
0.8627	High Similarity	NPC19380
0.8627	High Similarity	NPC146277
0.8618	High Similarity	NPC243891
0.8609	High Similarity	NPC476394
0.8609	High Similarity	NPC98809
0.8601	High Similarity	NPC475468
0.8592	High Similarity	NPC198388
0.8571	High Similarity	NPC100675
0.8562	High Similarity	NPC267091
0.8562	High Similarity	NPC142703
0.8562	High Similarity	NPC75695
0.8562	High Similarity	NPC219428
0.8562	High Similarity	NPC302857
0.8562	High Similarity	NPC37250
0.8562	High Similarity	NPC278068
0.8562	High Similarity	NPC152942
0.8543	High Similarity	NPC192568
0.8543	High Similarity	NPC471076
0.8542	High Similarity	NPC135127
0.8516	High Similarity	NPC145425
0.8514	High Similarity	NPC476842
0.8514	High Similarity	NPC476840
0.8497	Intermediate Similarity	NPC300329
0.8491	Intermediate Similarity	NPC134047
0.8491	Intermediate Similarity	NPC223006
0.8491	Intermediate Similarity	NPC272750
0.8491	Intermediate Similarity	NPC173729
0.8487	Intermediate Similarity	NPC478242
0.8483	Intermediate Similarity	NPC470990
0.8483	Intermediate Similarity	NPC113295
0.8477	Intermediate Similarity	NPC229264
0.8472	Intermediate Similarity	NPC159418
0.8472	Intermediate Similarity	NPC283823
0.8471	Intermediate Similarity	NPC76211
0.8471	Intermediate Similarity	NPC179914
0.8462	Intermediate Similarity	NPC469480
0.8462	Intermediate Similarity	NPC471405
0.8456	Intermediate Similarity	NPC277315
0.8456	Intermediate Similarity	NPC285550
0.8456	Intermediate Similarity	NPC220664
0.8456	Intermediate Similarity	NPC472016
0.8456	Intermediate Similarity	NPC192831
0.8456	Intermediate Similarity	NPC258469
0.8456	Intermediate Similarity	NPC37331
0.8456	Intermediate Similarity	NPC319628
0.8456	Intermediate Similarity	NPC43158
0.8456	Intermediate Similarity	NPC303090
0.8456	Intermediate Similarity	NPC284948
0.8446	Intermediate Similarity	NPC326065
0.8442	Intermediate Similarity	NPC476434
0.844	Intermediate Similarity	NPC281020
0.8431	Intermediate Similarity	NPC32197
0.8431	Intermediate Similarity	NPC221091
0.8431	Intermediate Similarity	NPC205054
0.8431	Intermediate Similarity	NPC259576
0.8431	Intermediate Similarity	NPC473091
0.8429	Intermediate Similarity	NPC280767
0.8428	Intermediate Similarity	NPC144557
0.8421	Intermediate Similarity	NPC294972
0.8418	Intermediate Similarity	NPC472961
0.8418	Intermediate Similarity	NPC44507
0.8418	Intermediate Similarity	NPC472962
0.8414	Intermediate Similarity	NPC300776
0.8414	Intermediate Similarity	NPC4982
0.8414	Intermediate Similarity	NPC5310
0.8414	Intermediate Similarity	NPC176814
0.8414	Intermediate Similarity	NPC37065
0.8414	Intermediate Similarity	NPC68779
0.8411	Intermediate Similarity	NPC287495
0.8411	Intermediate Similarity	NPC9370
0.8408	Intermediate Similarity	NPC40920
0.8408	Intermediate Similarity	NPC286919
0.8408	Intermediate Similarity	NPC223335
0.8408	Intermediate Similarity	NPC475663
0.8403	Intermediate Similarity	NPC111888
0.84	Intermediate Similarity	NPC183824
0.8397	Intermediate Similarity	NPC10205
0.8397	Intermediate Similarity	NPC38699
0.8392	Intermediate Similarity	NPC195292
0.8392	Intermediate Similarity	NPC142985
0.8389	Intermediate Similarity	NPC206095
0.8389	Intermediate Similarity	NPC297517
0.8389	Intermediate Similarity	NPC224389
0.8389	Intermediate Similarity	NPC35702
0.8389	Intermediate Similarity	NPC13818
0.8389	Intermediate Similarity	NPC477335
0.8389	Intermediate Similarity	NPC471027
0.838	Intermediate Similarity	NPC110313
0.8378	Intermediate Similarity	NPC156709
0.8378	Intermediate Similarity	NPC179505
0.8377	Intermediate Similarity	NPC178048
0.8366	Intermediate Similarity	NPC474903
0.8356	Intermediate Similarity	NPC233350
0.8356	Intermediate Similarity	NPC182217
0.8356	Intermediate Similarity	NPC70680
0.8354	Intermediate Similarity	NPC469384
0.8354	Intermediate Similarity	NPC469654
0.8345	Intermediate Similarity	NPC471749
0.8345	Intermediate Similarity	NPC327410
0.8344	Intermediate Similarity	NPC223185
0.8344	Intermediate Similarity	NPC113397
0.8333	Intermediate Similarity	NPC194095
0.8333	Intermediate Similarity	NPC477696
0.8333	Intermediate Similarity	NPC283041
0.8333	Intermediate Similarity	NPC470811
0.8333	Intermediate Similarity	NPC25127
0.8333	Intermediate Similarity	NPC106920
0.8333	Intermediate Similarity	NPC327032
0.8333	Intermediate Similarity	NPC287504
0.8333	Intermediate Similarity	NPC273657
0.8333	Intermediate Similarity	NPC191046
0.8333	Intermediate Similarity	NPC477697
0.8323	Intermediate Similarity	NPC203664
0.8323	Intermediate Similarity	NPC180586
0.8322	Intermediate Similarity	NPC9218
0.8322	Intermediate Similarity	NPC470991
0.8322	Intermediate Similarity	NPC304622
0.831	Intermediate Similarity	NPC293641
0.831	Intermediate Similarity	NPC20404
0.831	Intermediate Similarity	NPC151167
0.831	Intermediate Similarity	NPC123722
0.831	Intermediate Similarity	NPC276466
0.831	Intermediate Similarity	NPC12022
0.831	Intermediate Similarity	NPC5018
0.831	Intermediate Similarity	NPC123228
0.831	Intermediate Similarity	NPC20287
0.8291	Intermediate Similarity	NPC472860
0.8291	Intermediate Similarity	NPC226759
0.8289	Intermediate Similarity	NPC30890
0.8288	Intermediate Similarity	NPC474895
0.8288	Intermediate Similarity	NPC106406
0.8288	Intermediate Similarity	NPC68517
0.8286	Intermediate Similarity	NPC164778
0.8286	Intermediate Similarity	NPC257976

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 NPC98009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	878
0.2-0.3	1855
0.3-0.4	2557
0.4-0.5	1912
0.5-0.6	1083
0.6-0.7	496
0.7-0.8	83
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
0.8456	Intermediate Similarity	NPD6190	Approved
0.8113	Intermediate Similarity	NPD3882	Suspended
0.805	Intermediate Similarity	NPD3817	Phase 2
0.8026	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD9494	Approved
0.7917	Intermediate Similarity	NPD7685	Pre-registration
0.7902	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3818	Discontinued
0.7879	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6166	Phase 2
0.7879	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD230	Phase 1
0.784	Intermediate Similarity	NPD7075	Discontinued
0.7812	Intermediate Similarity	NPD6801	Discontinued
0.7812	Intermediate Similarity	NPD1934	Approved
0.7764	Intermediate Similarity	NPD2801	Approved
0.7751	Intermediate Similarity	NPD6797	Phase 2
0.7733	Intermediate Similarity	NPD6355	Discontinued
0.7706	Intermediate Similarity	NPD7251	Discontinued
0.7703	Intermediate Similarity	NPD3027	Phase 3
0.7683	Intermediate Similarity	NPD6234	Discontinued
0.7661	Intermediate Similarity	NPD7808	Phase 3
0.7654	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6798	Discontinued
0.7643	Intermediate Similarity	NPD6799	Approved
0.7633	Intermediate Similarity	NPD7054	Approved
0.761	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5402	Approved
0.7605	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7266	Discontinued
0.7593	Intermediate Similarity	NPD37	Approved
0.7588	Intermediate Similarity	NPD7074	Phase 3
0.7588	Intermediate Similarity	NPD7472	Approved
0.7578	Intermediate Similarity	NPD4380	Phase 2
0.7564	Intermediate Similarity	NPD8166	Discontinued
0.7564	Intermediate Similarity	NPD4110	Phase 3
0.7564	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1653	Approved
0.7561	Intermediate Similarity	NPD4965	Approved
0.7561	Intermediate Similarity	NPD4967	Phase 2
0.7561	Intermediate Similarity	NPD4966	Approved
0.755	Intermediate Similarity	NPD4060	Phase 1
0.7547	Intermediate Similarity	NPD1512	Approved
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7484	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3146	Approved
0.7483	Intermediate Similarity	NPD9545	Approved
0.7483	Intermediate Similarity	NPD4062	Phase 3
0.7483	Intermediate Similarity	NPD6233	Phase 2
0.7471	Intermediate Similarity	NPD7228	Approved
0.747	Intermediate Similarity	NPD919	Approved
0.7469	Intermediate Similarity	NPD6599	Discontinued
0.7466	Intermediate Similarity	NPD1608	Approved
0.744	Intermediate Similarity	NPD6232	Discontinued
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7436	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5844	Phase 1
0.7423	Intermediate Similarity	NPD6386	Approved
0.7423	Intermediate Similarity	NPD6385	Approved
0.7421	Intermediate Similarity	NPD1511	Approved
0.7413	Intermediate Similarity	NPD5536	Phase 2
0.741	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5401	Approved
0.7357	Intermediate Similarity	NPD228	Approved
0.7351	Intermediate Similarity	NPD7095	Approved
0.7326	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2354	Approved
0.7296	Intermediate Similarity	NPD3887	Approved
0.7289	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD4340	Discontinued
0.7273	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD3751	Discontinued
0.7267	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5647	Approved
0.7261	Intermediate Similarity	NPD5762	Approved
0.7261	Intermediate Similarity	NPD5763	Approved
0.726	Intermediate Similarity	NPD17	Approved
0.7244	Intermediate Similarity	NPD7033	Discontinued
0.7244	Intermediate Similarity	NPD1510	Phase 2
0.7233	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7819	Suspended
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5494	Approved
0.7215	Intermediate Similarity	NPD4534	Discontinued
0.7215	Intermediate Similarity	NPD5958	Discontinued
0.7208	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1613	Approved
0.7197	Intermediate Similarity	NPD2935	Discontinued
0.7195	Intermediate Similarity	NPD3455	Phase 2
0.7191	Intermediate Similarity	NPD8434	Phase 2
0.719	Intermediate Similarity	NPD3268	Approved
0.7176	Intermediate Similarity	NPD1247	Approved
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3787	Discontinued
0.7134	Intermediate Similarity	NPD2799	Discontinued
0.7133	Intermediate Similarity	NPD5283	Phase 1
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3750	Approved
0.7115	Intermediate Similarity	NPD6653	Approved
0.7114	Intermediate Similarity	NPD9269	Phase 2
0.7108	Intermediate Similarity	NPD7411	Suspended
0.7107	Intermediate Similarity	NPD1549	Phase 2
0.7097	Intermediate Similarity	NPD943	Approved
0.7097	Intermediate Similarity	NPD1240	Approved
0.7097	Intermediate Similarity	NPD3620	Phase 2
0.7097	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3926	Phase 2
0.7093	Intermediate Similarity	NPD5242	Approved
0.7091	Intermediate Similarity	NPD7458	Discontinued
0.7089	Intermediate Similarity	NPD2796	Approved
0.7089	Intermediate Similarity	NPD2438	Suspended
0.7086	Intermediate Similarity	NPD2797	Approved
0.7086	Intermediate Similarity	NPD987	Approved
0.7078	Intermediate Similarity	NPD3764	Approved
0.7071	Intermediate Similarity	NPD1358	Approved
0.7069	Intermediate Similarity	NPD2163	Approved
0.7055	Intermediate Similarity	NPD2532	Approved
0.7055	Intermediate Similarity	NPD2534	Approved
0.7055	Intermediate Similarity	NPD2533	Approved
0.7044	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2353	Approved
0.703	Intermediate Similarity	NPD3687	Approved
0.703	Intermediate Similarity	NPD3686	Approved
0.7027	Intermediate Similarity	NPD1778	Approved
0.7022	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1283	Approved
0.7014	Intermediate Similarity	NPD1241	Discontinued
0.7012	Intermediate Similarity	NPD6273	Approved
0.7006	Intermediate Similarity	NPD7039	Approved
0.7006	Intermediate Similarity	NPD7240	Approved
0.7006	Intermediate Similarity	NPD7038	Approved
0.7006	Intermediate Similarity	NPD6559	Discontinued
0.7006	Intermediate Similarity	NPD1607	Approved
0.7	Intermediate Similarity	NPD8150	Discontinued
0.7	Intermediate Similarity	NPD3134	Approved
0.6988	Remote Similarity	NPD3226	Approved
0.6987	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD825	Approved
0.6987	Remote Similarity	NPD826	Approved
0.6982	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2629	Approved
0.6966	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7097	Phase 1
0.6959	Remote Similarity	NPD5585	Approved
0.6959	Remote Similarity	NPD1357	Approved
0.6951	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7028	Phase 2
0.6944	Remote Similarity	NPD7843	Approved
0.6943	Remote Similarity	NPD5124	Phase 1
0.6943	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6004	Phase 3
0.6937	Remote Similarity	NPD6002	Phase 3
0.6937	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6005	Phase 3
0.6933	Remote Similarity	NPD3705	Approved
0.6933	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD422	Phase 1
0.6927	Remote Similarity	NPD8312	Approved
0.6927	Remote Similarity	NPD8313	Approved
0.6918	Remote Similarity	NPD7157	Approved
0.6918	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4626	Approved
0.6909	Remote Similarity	NPD5049	Phase 3
0.6905	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2684	Approved
0.6895	Remote Similarity	NPD4582	Approved
0.6895	Remote Similarity	NPD4583	Approved
0.6894	Remote Similarity	NPD2424	Discontinued
0.6892	Remote Similarity	NPD1894	Discontinued
0.689	Remote Similarity	NPD4357	Discontinued
0.6889	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3972	Approved
0.6886	Remote Similarity	NPD824	Approved
0.6885	Remote Similarity	NPD2488	Approved
0.6885	Remote Similarity	NPD2490	Approved
0.6883	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD6100	Approved
0.6875	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6099	Approved
0.6867	Remote Similarity	NPD3847	Discontinued
0.6867	Remote Similarity	NPD3496	Discontinued
0.6863	Remote Similarity	NPD3266	Approved

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