NPASS Compound

Structure

CID49597 OpenBabel06191715382D 36 39 0 0 1 0 0 0 0 0999 V2000 2.5602 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3738 -1.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5328 -0.1984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8386 0.1617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1170 -2.1547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2760 -0.8675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0465 1.1399 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5817 -0.5074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0680 -1.8457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3034 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8112 -2.5148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 3.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5113 2.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 2.1045 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 5 1 0 0 0 0 2 12 2 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 24 1 0 0 0 0 9 33 1 0 0 0 0 10 15 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 0 0 0 0 13 26 1 0 0 0 0 14 11 1 1 0 0 0 14 17 1 0 0 0 0 14 34 1 0 0 0 0 15 24 1 6 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 16 36 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 6 0 0 0 18 19 1 0 0 0 0 18 30 1 1 0 0 0 19 21 1 0 0 0 0 19 31 1 6 0 0 0 20 22 1 0 0 0 0 20 23 1 1 0 0 0 20 24 1 0 0 0 0 21 34 1 0 0 0 0 21 35 1 1 0 0 0 22 33 1 0 0 0 0 22 35 1 6 0 0 0 23 1 1 1 0 0 0 23 36 1 0 0 0 0 24 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.17
Volume:	479.098
LogP:	0.404
LogD:	-0.222
LogS:	-2.68
# Rotatable Bonds:	7
TPSA:	195.6
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.173
Synthetic Accessibility Score:	4.946
Fsp3:	0.542
Lipinski Rule-of-5:	Rejected
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:	-6.379
MDCK Permeability:	5.626748315989971e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.953
Human Intestinal Absorption (HIA):	0.48
20% Bioavailability (F20%):	0.876
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.149
Plasma Protein Binding (PPB):	68.65837860107422%
Volume Distribution (VD):	0.389
Pgp-substrate:	29.894760131835938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.203
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	1.155
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.393
Maximum Recommended Daily Dose:	0.361
Skin Sensitization:	0.606
Carcinogencity:	0.884
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC49597

Natural Product ID:	NPC49597
*Common Name:**	8-Coumaroylharpagide
IUPAC Name:	[(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:	8-Coumaroylharpagide
Standard InCHIKey:	AZKQDXZMKREFDY-CBLWINFVSA-N
Standard InCHI:	InChI=1S/C24H30O12/c1-23(36-16(28)7-4-12-2-5-13(26)6-3-12)10-15(27)24(32)8-9-33-22(20(23)24)35-21-19(31)18(30)17(29)14(11-25)34-21/h2-9,14-15,17-22,25-27,29-32H,10-11H2,1H3/b7-4+/t14-,15-,17-,18+,19-,20-,21+,22+,23+,24-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@]3([C@H]2[C@@](C)(OC(=O)/C=C/c2ccc(cc2)O)C[C@H]3O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513852
PubChem CID:	10324058
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2688	Organism	Sus scrofa	Sus scrofa	Inhibition	<	50.0	%	PMID[503818]

☑ 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 NPC49597 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	285
0.1-0.2	1150
0.2-0.3	2856
0.3-0.4	6745
0.4-0.5	10788
0.5-0.6	10967
0.6-0.7	8394
0.7-0.8	1312
0.8-0.85	135
0.85-0.9	33
0.9-0.95	22
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC46644
0.9559	High Similarity	NPC263397
0.9559	High Similarity	NPC302286
0.9559	High Similarity	NPC88754
0.9559	High Similarity	NPC116104
0.9559	High Similarity	NPC237872
0.9489	High Similarity	NPC184464
0.9489	High Similarity	NPC251062
0.9412	High Similarity	NPC137501
0.9412	High Similarity	NPC7518
0.9412	High Similarity	NPC154262
0.9412	High Similarity	NPC159387
0.9353	High Similarity	NPC37838
0.9348	High Similarity	NPC478240
0.9318	High Similarity	NPC254819
0.9286	High Similarity	NPC18789
0.9275	High Similarity	NPC186296
0.9155	High Similarity	NPC478234
0.9091	High Similarity	NPC240592
0.9091	High Similarity	NPC117346
0.9091	High Similarity	NPC147224
0.9084	High Similarity	NPC267733
0.9084	High Similarity	NPC276047
0.9034	High Similarity	NPC229548
0.9034	High Similarity	NPC478241
0.9034	High Similarity	NPC89693
0.903	High Similarity	NPC475824
0.9028	High Similarity	NPC269914
0.9028	High Similarity	NPC478249
0.9021	High Similarity	NPC478236
0.9021	High Similarity	NPC96599
0.8986	High Similarity	NPC31745
0.8986	High Similarity	NPC220936
0.8966	High Similarity	NPC194705
0.8951	High Similarity	NPC308178
0.8936	High Similarity	NPC202391
0.8936	High Similarity	NPC296659
0.8931	High Similarity	NPC145287
0.8897	High Similarity	NPC289021
0.8897	High Similarity	NPC158546
0.8872	High Similarity	NPC106677
0.8851	High Similarity	NPC475378
0.8797	High Similarity	NPC471157
0.8797	High Similarity	NPC252114
0.8779	High Similarity	NPC52097
0.875	High Similarity	NPC478255
0.8741	High Similarity	NPC253595
0.8732	High Similarity	NPC293154
0.8731	High Similarity	NPC156692
0.8731	High Similarity	NPC35288
0.8731	High Similarity	NPC175333
0.8731	High Similarity	NPC471882
0.8731	High Similarity	NPC173150
0.8731	High Similarity	NPC45224
0.8731	High Similarity	NPC471881
0.8731	High Similarity	NPC288416
0.8725	High Similarity	NPC478248
0.8722	High Similarity	NPC83218
0.8722	High Similarity	NPC126991
0.8716	High Similarity	NPC478232
0.8705	High Similarity	NPC472132
0.8702	High Similarity	NPC11724
0.8696	High Similarity	NPC169398
0.8675	High Similarity	NPC478265
0.8671	High Similarity	NPC77922
0.8671	High Similarity	NPC473281
0.8667	High Similarity	NPC225307
0.8658	High Similarity	NPC475484
0.8657	High Similarity	NPC61181
0.8649	High Similarity	NPC229354
0.8639	High Similarity	NPC475379
0.8626	High Similarity	NPC476872
0.8613	High Similarity	NPC225384
0.8613	High Similarity	NPC138777
0.8613	High Similarity	NPC246869
0.8613	High Similarity	NPC235294
0.8613	High Similarity	NPC46137
0.8601	High Similarity	NPC475213
0.8601	High Similarity	NPC152796
0.8593	High Similarity	NPC103533
0.8581	High Similarity	NPC478235
0.8553	High Similarity	NPC138993
0.8552	High Similarity	NPC474268
0.8552	High Similarity	NPC143246
0.8552	High Similarity	NPC475539
0.8552	High Similarity	NPC474234
0.8552	High Similarity	NPC119773
0.8542	High Similarity	NPC63304
0.8511	High Similarity	NPC101686
0.8511	High Similarity	NPC469364
0.8511	High Similarity	NPC65262
0.8493	Intermediate Similarity	NPC473149
0.8489	Intermediate Similarity	NPC254398
0.8483	Intermediate Similarity	NPC475528
0.8478	Intermediate Similarity	NPC281798
0.8467	Intermediate Similarity	NPC295970
0.8442	Intermediate Similarity	NPC476011
0.8417	Intermediate Similarity	NPC473924
0.8417	Intermediate Similarity	NPC473285
0.8397	Intermediate Similarity	NPC301910
0.8397	Intermediate Similarity	NPC130730
0.8369	Intermediate Similarity	NPC263829
0.8369	Intermediate Similarity	NPC476870
0.8366	Intermediate Similarity	NPC179914
0.8357	Intermediate Similarity	NPC28637
0.8355	Intermediate Similarity	NPC478266
0.8345	Intermediate Similarity	NPC219677
0.8333	Intermediate Similarity	NPC477293
0.8333	Intermediate Similarity	NPC229784
0.8333	Intermediate Similarity	NPC477294
0.8323	Intermediate Similarity	NPC206815
0.8322	Intermediate Similarity	NPC69367
0.8322	Intermediate Similarity	NPC321184
0.8322	Intermediate Similarity	NPC35097
0.8322	Intermediate Similarity	NPC328273
0.8322	Intermediate Similarity	NPC321638
0.8322	Intermediate Similarity	NPC171134
0.8312	Intermediate Similarity	NPC474936
0.831	Intermediate Similarity	NPC166180
0.8299	Intermediate Similarity	NPC473147
0.8298	Intermediate Similarity	NPC34293
0.8298	Intermediate Similarity	NPC287597
0.8298	Intermediate Similarity	NPC471883
0.8298	Intermediate Similarity	NPC886
0.8288	Intermediate Similarity	NPC194938
0.8278	Intermediate Similarity	NPC469699
0.8276	Intermediate Similarity	NPC296643
0.8269	Intermediate Similarity	NPC109990
0.8267	Intermediate Similarity	NPC474620
0.8261	Intermediate Similarity	NPC232880
0.8252	Intermediate Similarity	NPC476376
0.8228	Intermediate Similarity	NPC208818
0.8227	Intermediate Similarity	NPC470143
0.8227	Intermediate Similarity	NPC322503
0.8219	Intermediate Similarity	NPC204644
0.8212	Intermediate Similarity	NPC203664
0.8209	Intermediate Similarity	NPC476448
0.8209	Intermediate Similarity	NPC476445
0.8209	Intermediate Similarity	NPC469548
0.8207	Intermediate Similarity	NPC215512
0.8207	Intermediate Similarity	NPC476442
0.8205	Intermediate Similarity	NPC145847
0.8194	Intermediate Similarity	NPC89105
0.8194	Intermediate Similarity	NPC472350
0.8194	Intermediate Similarity	NPC476383
0.8194	Intermediate Similarity	NPC68092
0.8194	Intermediate Similarity	NPC197316
0.8194	Intermediate Similarity	NPC81515
0.8194	Intermediate Similarity	NPC226005
0.8194	Intermediate Similarity	NPC64141
0.8194	Intermediate Similarity	NPC269668
0.8188	Intermediate Similarity	NPC120728
0.8188	Intermediate Similarity	NPC189631
0.8188	Intermediate Similarity	NPC476873
0.8182	Intermediate Similarity	NPC157554
0.8182	Intermediate Similarity	NPC471345
0.8182	Intermediate Similarity	NPC329997
0.8176	Intermediate Similarity	NPC212808
0.8163	Intermediate Similarity	NPC110063
0.8163	Intermediate Similarity	NPC196063
0.8163	Intermediate Similarity	NPC296954
0.8163	Intermediate Similarity	NPC300894
0.8163	Intermediate Similarity	NPC141455
0.8158	Intermediate Similarity	NPC257847
0.8151	Intermediate Similarity	NPC140502
0.8146	Intermediate Similarity	NPC77310
0.8134	Intermediate Similarity	NPC282409
0.8134	Intermediate Similarity	NPC469702
0.8133	Intermediate Similarity	NPC161955
0.8129	Intermediate Similarity	NPC146540
0.8125	Intermediate Similarity	NPC78363
0.8125	Intermediate Similarity	NPC260425
0.8121	Intermediate Similarity	NPC97240
0.8106	Intermediate Similarity	NPC175771
0.8106	Intermediate Similarity	NPC148055
0.8099	Intermediate Similarity	NPC114116
0.8095	Intermediate Similarity	NPC478250
0.8095	Intermediate Similarity	NPC478239
0.8095	Intermediate Similarity	NPC40305
0.8095	Intermediate Similarity	NPC105005
0.8092	Intermediate Similarity	NPC313193
0.8082	Intermediate Similarity	NPC476385
0.8082	Intermediate Similarity	NPC186406
0.8082	Intermediate Similarity	NPC476377
0.8082	Intermediate Similarity	NPC134405
0.8082	Intermediate Similarity	NPC47471
0.8077	Intermediate Similarity	NPC208676
0.8077	Intermediate Similarity	NPC130489
0.8071	Intermediate Similarity	NPC469549
0.8069	Intermediate Similarity	NPC220942
0.8069	Intermediate Similarity	NPC100389
0.8069	Intermediate Similarity	NPC205195
0.8067	Intermediate Similarity	NPC169510
0.8065	Intermediate Similarity	NPC187205
0.8063	Intermediate Similarity	NPC21956
0.8056	Intermediate Similarity	NPC103409
0.8056	Intermediate Similarity	NPC37468
0.8056	Intermediate Similarity	NPC470572
0.8054	Intermediate Similarity	NPC320734
0.8054	Intermediate Similarity	NPC229505

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 NPC49597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	714
0.2-0.3	1655
0.3-0.4	2915
0.4-0.5	2169
0.5-0.6	1205
0.6-0.7	247
0.7-0.8	14
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
0.8194	Intermediate Similarity	NPD7266	Discontinued
0.8137	Intermediate Similarity	NPD7685	Pre-registration
0.7662	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD1091	Approved
0.7315	Intermediate Similarity	NPD6653	Approved
0.7292	Intermediate Similarity	NPD3094	Phase 2
0.7273	Intermediate Similarity	NPD6190	Approved
0.7178	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7133	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5124	Phase 1
0.7124	Intermediate Similarity	NPD5762	Approved
0.7124	Intermediate Similarity	NPD5763	Approved
0.7123	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD969	Suspended
0.7055	Intermediate Similarity	NPD6362	Approved
0.7039	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7097	Phase 1
0.7037	Intermediate Similarity	NPD1358	Approved
0.7014	Intermediate Similarity	NPD3092	Approved
0.7013	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6005	Phase 3
0.7013	Intermediate Similarity	NPD6004	Phase 3
0.7013	Intermediate Similarity	NPD6002	Phase 3
0.7011	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5647	Approved
0.6994	Remote Similarity	NPD8455	Phase 2
0.6987	Remote Similarity	NPD4628	Phase 3
0.6972	Remote Similarity	NPD9545	Approved
0.6963	Remote Similarity	NPD3134	Approved
0.6959	Remote Similarity	NPD2861	Phase 2
0.6959	Remote Similarity	NPD5736	Approved
0.6954	Remote Similarity	NPD4140	Approved
0.6946	Remote Similarity	NPD7199	Phase 2
0.6941	Remote Similarity	NPD7228	Approved
0.6933	Remote Similarity	NPD37	Approved
0.6928	Remote Similarity	NPD6234	Discontinued
0.6909	Remote Similarity	NPD4967	Phase 2
0.6909	Remote Similarity	NPD4965	Approved
0.6909	Remote Similarity	NPD4966	Approved
0.6908	Remote Similarity	NPD4340	Discontinued
0.6899	Remote Similarity	NPD5058	Phase 3
0.6897	Remote Similarity	NPD422	Phase 1
0.6883	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD6559	Discontinued
0.6875	Remote Similarity	NPD5126	Approved
0.6875	Remote Similarity	NPD5125	Phase 3
0.6855	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3818	Discontinued
0.6821	Remote Similarity	NPD3764	Approved
0.681	Remote Similarity	NPD4380	Phase 2
0.6802	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7054	Approved
0.6797	Remote Similarity	NPD5735	Approved
0.6797	Remote Similarity	NPD6355	Discontinued
0.6781	Remote Similarity	NPD3705	Approved
0.6776	Remote Similarity	NPD6663	Approved
0.6776	Remote Similarity	NPD6233	Phase 2
0.6765	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7472	Approved
0.6755	Remote Similarity	NPD3027	Phase 3
0.6746	Remote Similarity	NPD8127	Discontinued
0.6744	Remote Similarity	NPD7799	Discontinued
0.6743	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3091	Approved
0.6732	Remote Similarity	NPD3620	Phase 2
0.6732	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4060	Phase 1
0.6724	Remote Similarity	NPD6797	Phase 2
0.6709	Remote Similarity	NPD6674	Discontinued
0.6707	Remote Similarity	NPD7028	Phase 2
0.6705	Remote Similarity	NPD8313	Approved
0.6705	Remote Similarity	NPD8312	Approved
0.669	Remote Similarity	NPD1357	Approved
0.6689	Remote Similarity	NPD4908	Phase 1
0.6688	Remote Similarity	NPD230	Phase 1
0.6686	Remote Similarity	NPD7251	Discontinued
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD7843	Approved
0.6648	Remote Similarity	NPD7808	Phase 3
0.6646	Remote Similarity	NPD2424	Discontinued
0.6643	Remote Similarity	NPD7157	Approved
0.663	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6801	Discontinued
0.6626	Remote Similarity	NPD5403	Approved
0.6623	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1613	Approved
0.6621	Remote Similarity	NPD7741	Discontinued
0.6619	Remote Similarity	NPD2684	Approved
0.6618	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6798	Discontinued
0.6601	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2797	Approved
0.6597	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6685	Approved
0.6591	Remote Similarity	NPD7240	Approved
0.6577	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7503	Approved
0.6564	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8166	Discontinued
0.6562	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1610	Phase 2
0.6547	Remote Similarity	NPD290	Approved
0.6545	Remote Similarity	NPD7458	Discontinued
0.6536	Remote Similarity	NPD7095	Approved
0.6533	Remote Similarity	NPD3225	Approved
0.6531	Remote Similarity	NPD3095	Discontinued
0.6524	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD1548	Phase 1
0.6503	Remote Similarity	NPD5401	Approved
0.6503	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4538	Approved
0.6497	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4536	Approved
0.6494	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3268	Approved
0.6488	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3496	Discontinued
0.646	Remote Similarity	NPD3750	Approved
0.6456	Remote Similarity	NPD5588	Approved
0.6452	Remote Similarity	NPD4062	Phase 3
0.645	Remote Similarity	NPD5402	Approved
0.6447	Remote Similarity	NPD4624	Approved
0.6442	Remote Similarity	NPD6799	Approved
0.6438	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5535	Approved
0.6433	Remote Similarity	NPD6353	Approved
0.6424	Remote Similarity	NPD8651	Approved
0.6419	Remote Similarity	NPD4626	Approved
0.6419	Remote Similarity	NPD4059	Approved
0.6414	Remote Similarity	NPD4198	Discontinued
0.6402	Remote Similarity	NPD3536	Discontinued
0.6398	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD3020	Approved
0.6387	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.638	Remote Similarity	NPD7236	Approved
0.6377	Remote Similarity	NPD6647	Phase 2
0.6377	Remote Similarity	NPD5765	Approved
0.637	Remote Similarity	NPD9493	Approved
0.6369	Remote Similarity	NPD1933	Approved
0.6369	Remote Similarity	NPD7411	Suspended
0.6364	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3751	Discontinued
0.6364	Remote Similarity	NPD6912	Phase 3
0.6358	Remote Similarity	NPD4110	Phase 3
0.6358	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5327	Phase 3
0.6358	Remote Similarity	NPD4749	Approved
0.6358	Remote Similarity	NPD3685	Discontinued
0.6353	Remote Similarity	NPD3817	Phase 2
0.6352	Remote Similarity	NPD4108	Discontinued
0.6352	Remote Similarity	NPD5960	Phase 3
0.6351	Remote Similarity	NPD5691	Approved
0.6345	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD2934	Approved
0.6343	Remote Similarity	NPD2933	Approved
0.6338	Remote Similarity	NPD3021	Approved
0.6338	Remote Similarity	NPD3022	Approved
0.6335	Remote Similarity	NPD1549	Phase 2
0.6335	Remote Similarity	NPD5958	Discontinued
0.6331	Remote Similarity	NPD1934	Approved
0.6328	Remote Similarity	NPD5844	Phase 1
0.6323	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD2935	Discontinued
0.6312	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.631	Remote Similarity	NPD6599	Discontinued
0.6309	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2859	Approved
0.6296	Remote Similarity	NPD2860	Approved
0.6294	Remote Similarity	NPD5761	Phase 2
0.6294	Remote Similarity	NPD7930	Approved
0.6294	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5760	Phase 2
0.6294	Remote Similarity	NPD7819	Suspended
0.6287	Remote Similarity	NPD7239	Suspended
0.6286	Remote Similarity	NPD9697	Approved
0.6283	Remote Similarity	NPD7435	Discontinued
0.6283	Remote Similarity	NPD7497	Discontinued
0.6278	Remote Similarity	NPD7549	Discontinued
0.6275	Remote Similarity	NPD987	Approved
0.6273	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD3847	Discontinued
0.6258	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD2415	Discontinued
0.6257	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6166	Phase 2

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