NPASS Compound

Structure

NPC134227 OpenBabel07101718282D 21 24 0 0 1 0 0 0 0 0999 V2000 0.0456 -1.0482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2430 1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2646 2.1338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6921 1.8701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1622 1.5428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3553 1.4603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9582 1.6071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7757 1.3435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7062 -1.0482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8759 -0.5688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5365 -0.5688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6415 0.7125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5365 0.3900 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0119 -0.0894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4484 0.6862 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7062 0.8693 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8759 0.3900 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5951 0.6123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9707 -0.0894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4484 -0.8651 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 10 1 0 0 0 0 3 16 1 0 0 0 0 4 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 9 10 1 0 0 0 0 10 17 1 1 0 0 0 11 9 1 6 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 15 1 6 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 2 1 1 0 0 0 16 17 1 1 0 0 0 17 8 1 6 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.17
Volume:	298.25
LogP:	2.739
LogD:	2.601
LogS:	-4.353
# Rotatable Bonds:	0
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	5.061
Fsp3:	0.882
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.249
MDCK Permeability:	1.9167231585015543e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.117
30% Bioavailability (F30%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.119
Plasma Protein Binding (PPB):	54.96300506591797%
Volume Distribution (VD):	0.583
Pgp-substrate:	42.20344924926758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.443
CYP2C19-inhibitor:	0.143
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.814
CYP3A4-substrate:	0.517

ADMET: Excretion

Clearance (CL):	10.81
Half-life (T1/2):	0.464

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.571
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.202
Maximum Recommended Daily Dose:	0.595
Skin Sensitization:	0.928
Carcinogencity:	0.562
Eye Corrosion:	0.053
Eye Irritation:	0.158
Respiratory Toxicity:	0.099

Download Data

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

Natural Product: NPC134227

Natural Product ID:	NPC134227
*Common Name:**	DFQREMVEHMYQMW-MZIBEIOLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DFQREMVEHMYQMW-MZIBEIOLSA-N
Standard InCHI:	InChI=1S/C17H24O4/c1-10-9-11-13-15(2,14(19)20-11)6-4-7-16(13,3)17(10)8-5-12(18)21-17/h10-11,13H,4-9H2,1-3H3/t10-,11-,13+,15+,16+,17-/m1/s1
SMILES:	O=C1CC[C@@]2(O1)[C@H](C)C[C@@H]1[C@@H]3[C@]2(C)CCC[C@]3(C)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078053
PubChem CID:	46883095
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO33187	marrubium globosum ssp. libanoticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19650652]

☑ 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
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6562	Tissue	Ileum	Mus musculus	Inhibition	>	50.0	%	PMID[551933]

☑ 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 NPC134227 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	394
0.1-0.2	3655
0.2-0.3	9813
0.3-0.4	13356
0.4-0.5	5712
0.5-0.6	6907
0.6-0.7	2408
0.7-0.8	409
0.8-0.85	32
0.85-0.9	8
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC125366
0.9189	High Similarity	NPC55508
0.9054	High Similarity	NPC109510
0.9	High Similarity	NPC65133
0.8831	High Similarity	NPC143250
0.8571	High Similarity	NPC471221
0.8554	High Similarity	NPC477441
0.8415	Intermediate Similarity	NPC15091
0.8354	Intermediate Similarity	NPC307865
0.8353	Intermediate Similarity	NPC476435
0.8353	Intermediate Similarity	NPC221993
0.8313	Intermediate Similarity	NPC477434
0.8276	Intermediate Similarity	NPC216137
0.8276	Intermediate Similarity	NPC475878
0.8256	Intermediate Similarity	NPC477440
0.8256	Intermediate Similarity	NPC477443
0.8243	Intermediate Similarity	NPC84562
0.8222	Intermediate Similarity	NPC266417
0.8171	Intermediate Similarity	NPC475743
0.8161	Intermediate Similarity	NPC477442
0.8161	Intermediate Similarity	NPC477444
0.8161	Intermediate Similarity	NPC477433
0.8148	Intermediate Similarity	NPC474754
0.8095	Intermediate Similarity	NPC473299
0.809	Intermediate Similarity	NPC470424
0.8077	Intermediate Similarity	NPC474755
0.8068	Intermediate Similarity	NPC474065
0.8046	Intermediate Similarity	NPC200580
0.8046	Intermediate Similarity	NPC67653
0.8046	Intermediate Similarity	NPC471459
0.8	Intermediate Similarity	NPC477445
0.8	Intermediate Similarity	NPC471046
0.7978	Intermediate Similarity	NPC147272
0.7955	Intermediate Similarity	NPC470114
0.7952	Intermediate Similarity	NPC71541
0.7952	Intermediate Similarity	NPC328639
0.7952	Intermediate Similarity	NPC329490
0.7935	Intermediate Similarity	NPC472144
0.7927	Intermediate Similarity	NPC73013
0.7912	Intermediate Similarity	NPC475785
0.7912	Intermediate Similarity	NPC475765
0.7889	Intermediate Similarity	NPC477495
0.7882	Intermediate Similarity	NPC181871
0.7882	Intermediate Similarity	NPC9060
0.7857	Intermediate Similarity	NPC13494
0.7831	Intermediate Similarity	NPC1882
0.7831	Intermediate Similarity	NPC471217
0.7831	Intermediate Similarity	NPC471216
0.7826	Intermediate Similarity	NPC472145
0.7826	Intermediate Similarity	NPC474921
0.7816	Intermediate Similarity	NPC239938
0.7791	Intermediate Similarity	NPC473350
0.7791	Intermediate Similarity	NPC474572
0.7778	Intermediate Similarity	NPC474379
0.7765	Intermediate Similarity	NPC476721
0.7753	Intermediate Similarity	NPC472146
0.7753	Intermediate Similarity	NPC185529
0.7738	Intermediate Similarity	NPC58631
0.7727	Intermediate Similarity	NPC236459
0.7717	Intermediate Similarity	NPC235109
0.7717	Intermediate Similarity	NPC193785
0.7711	Intermediate Similarity	NPC477287
0.7703	Intermediate Similarity	NPC306750
0.7701	Intermediate Similarity	NPC474008
0.7701	Intermediate Similarity	NPC248216
0.7701	Intermediate Similarity	NPC476717
0.7684	Intermediate Similarity	NPC213528
0.7684	Intermediate Similarity	NPC244969
0.7674	Intermediate Similarity	NPC219535
0.7674	Intermediate Similarity	NPC237938
0.764	Intermediate Similarity	NPC61688
0.764	Intermediate Similarity	NPC472234
0.764	Intermediate Similarity	NPC472233
0.7619	Intermediate Similarity	NPC60568
0.7614	Intermediate Similarity	NPC470920
0.7614	Intermediate Similarity	NPC175293
0.7609	Intermediate Similarity	NPC56369
0.7609	Intermediate Similarity	NPC90014
0.7609	Intermediate Similarity	NPC82633
0.759	Intermediate Similarity	NPC475725
0.7586	Intermediate Similarity	NPC476715
0.7586	Intermediate Similarity	NPC477205
0.7582	Intermediate Similarity	NPC476189
0.7568	Intermediate Similarity	NPC478126
0.7561	Intermediate Similarity	NPC474020
0.7561	Intermediate Similarity	NPC92489
0.7556	Intermediate Similarity	NPC475776
0.7556	Intermediate Similarity	NPC77756
0.7553	Intermediate Similarity	NPC253995
0.7531	Intermediate Similarity	NPC96759
0.7529	Intermediate Similarity	NPC470154
0.7529	Intermediate Similarity	NPC48756
0.7529	Intermediate Similarity	NPC280781
0.7529	Intermediate Similarity	NPC470156
0.7529	Intermediate Similarity	NPC476071
0.7528	Intermediate Similarity	NPC477614
0.7528	Intermediate Similarity	NPC476379
0.7528	Intermediate Similarity	NPC131104
0.7528	Intermediate Similarity	NPC473319
0.7528	Intermediate Similarity	NPC3032
0.7528	Intermediate Similarity	NPC226491
0.7527	Intermediate Similarity	NPC473964
0.7527	Intermediate Similarity	NPC116683
0.7527	Intermediate Similarity	NPC256227
0.7527	Intermediate Similarity	NPC163685
0.7526	Intermediate Similarity	NPC100078
0.75	Intermediate Similarity	NPC80700
0.75	Intermediate Similarity	NPC83242
0.75	Intermediate Similarity	NPC201276
0.75	Intermediate Similarity	NPC472272
0.75	Intermediate Similarity	NPC80891
0.7473	Intermediate Similarity	NPC52756
0.7471	Intermediate Similarity	NPC473336
0.7471	Intermediate Similarity	NPC18953
0.7471	Intermediate Similarity	NPC475689
0.7471	Intermediate Similarity	NPC471044
0.7471	Intermediate Similarity	NPC291310
0.7471	Intermediate Similarity	NPC97505
0.747	Intermediate Similarity	NPC471151
0.7468	Intermediate Similarity	NPC295788
0.7449	Intermediate Similarity	NPC306776
0.7449	Intermediate Similarity	NPC166079
0.7447	Intermediate Similarity	NPC473963
0.7442	Intermediate Similarity	NPC102156
0.7442	Intermediate Similarity	NPC148740
0.7442	Intermediate Similarity	NPC477446
0.7442	Intermediate Similarity	NPC100366
0.7442	Intermediate Similarity	NPC242771
0.7442	Intermediate Similarity	NPC477284
0.7442	Intermediate Similarity	NPC470155
0.7442	Intermediate Similarity	NPC164289
0.7442	Intermediate Similarity	NPC311642
0.7442	Intermediate Similarity	NPC477447
0.7436	Intermediate Similarity	NPC41542
0.7419	Intermediate Similarity	NPC217329
0.7419	Intermediate Similarity	NPC287354
0.7419	Intermediate Similarity	NPC62407
0.7416	Intermediate Similarity	NPC110365
0.7416	Intermediate Similarity	NPC213658
0.7416	Intermediate Similarity	NPC62202
0.7416	Intermediate Similarity	NPC45833
0.7412	Intermediate Similarity	NPC472943
0.7412	Intermediate Similarity	NPC477851
0.7412	Intermediate Similarity	NPC472951
0.7407	Intermediate Similarity	NPC123122
0.7396	Intermediate Similarity	NPC475958
0.7391	Intermediate Similarity	NPC161035
0.7391	Intermediate Similarity	NPC472232
0.7391	Intermediate Similarity	NPC472231
0.7386	Intermediate Similarity	NPC235402
0.7386	Intermediate Similarity	NPC62572
0.7386	Intermediate Similarity	NPC478111
0.7381	Intermediate Similarity	NPC34046
0.7381	Intermediate Similarity	NPC80089
0.7381	Intermediate Similarity	NPC224802
0.7381	Intermediate Similarity	NPC171426
0.7381	Intermediate Similarity	NPC324700
0.7368	Intermediate Similarity	NPC476807
0.7368	Intermediate Similarity	NPC476806
0.7368	Intermediate Similarity	NPC474724
0.7363	Intermediate Similarity	NPC18536
0.7363	Intermediate Similarity	NPC88337
0.7363	Intermediate Similarity	NPC475211
0.7363	Intermediate Similarity	NPC50443
0.7347	Intermediate Similarity	NPC88469
0.7347	Intermediate Similarity	NPC473701
0.7347	Intermediate Similarity	NPC473526
0.734	Intermediate Similarity	NPC476728
0.734	Intermediate Similarity	NPC200054
0.734	Intermediate Similarity	NPC29410
0.734	Intermediate Similarity	NPC93245
0.7333	Intermediate Similarity	NPC204173
0.7326	Intermediate Similarity	NPC271572
0.7326	Intermediate Similarity	NPC474870
0.7326	Intermediate Similarity	NPC475951
0.732	Intermediate Similarity	NPC471254
0.7312	Intermediate Similarity	NPC309127
0.7312	Intermediate Similarity	NPC474841
0.7312	Intermediate Similarity	NPC471446
0.7312	Intermediate Similarity	NPC473434
0.7312	Intermediate Similarity	NPC247877
0.7303	Intermediate Similarity	NPC475729
0.7303	Intermediate Similarity	NPC120395
0.7303	Intermediate Similarity	NPC243746
0.7303	Intermediate Similarity	NPC474215
0.7294	Intermediate Similarity	NPC476176
0.7294	Intermediate Similarity	NPC320144
0.7292	Intermediate Similarity	NPC267921
0.7284	Intermediate Similarity	NPC197701
0.7283	Intermediate Similarity	NPC165180
0.7283	Intermediate Similarity	NPC470230
0.7273	Intermediate Similarity	NPC101138
0.7273	Intermediate Similarity	NPC79308
0.7273	Intermediate Similarity	NPC25802
0.7273	Intermediate Similarity	NPC82492
0.7273	Intermediate Similarity	NPC51135
0.7263	Intermediate Similarity	NPC253586
0.7263	Intermediate Similarity	NPC471241
0.7263	Intermediate Similarity	NPC469810
0.7262	Intermediate Similarity	NPC207010

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 NPC134227 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	3817
0.2-0.3	3289
0.3-0.4	992
0.4-0.5	285
0.5-0.6	239
0.6-0.7	97
0.7-0.8	11
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
0.7396	Intermediate Similarity	NPD1700	Approved
0.7381	Intermediate Similarity	NPD6115	Approved
0.7381	Intermediate Similarity	NPD6118	Approved
0.7381	Intermediate Similarity	NPD6114	Approved
0.7381	Intermediate Similarity	NPD6697	Approved
0.7273	Intermediate Similarity	NPD6008	Approved
0.7262	Intermediate Similarity	NPD6116	Phase 1
0.7229	Intermediate Similarity	NPD3703	Phase 2
0.7143	Intermediate Similarity	NPD6117	Approved
0.7126	Intermediate Similarity	NPD1779	Approved
0.7126	Intermediate Similarity	NPD1780	Approved
0.7125	Intermediate Similarity	NPD229	Approved
0.7073	Intermediate Similarity	NPD5777	Approved
0.7024	Intermediate Similarity	NPD3702	Approved
0.6905	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.675	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD8035	Phase 2
0.6737	Remote Similarity	NPD8034	Phase 2
0.6699	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4224	Phase 2
0.6429	Remote Similarity	NPD7900	Approved
0.6429	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3669	Approved
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6399	Phase 3
0.6321	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD3573	Approved
0.631	Remote Similarity	NPD5360	Phase 3
0.631	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5739	Approved
0.6286	Remote Similarity	NPD6675	Approved
0.6286	Remote Similarity	NPD7128	Approved
0.6286	Remote Similarity	NPD6402	Approved
0.6279	Remote Similarity	NPD6081	Approved
0.6277	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6928	Phase 2
0.6262	Remote Similarity	NPD6372	Approved
0.6262	Remote Similarity	NPD6373	Approved
0.6238	Remote Similarity	NPD7902	Approved
0.6235	Remote Similarity	NPD3698	Phase 2
0.6226	Remote Similarity	NPD5701	Approved
0.6226	Remote Similarity	NPD5697	Approved
0.6182	Remote Similarity	NPD4632	Approved
0.6176	Remote Similarity	NPD7638	Approved
0.6168	Remote Similarity	NPD6899	Approved
0.6168	Remote Similarity	NPD6011	Approved
0.6168	Remote Similarity	NPD6881	Approved
0.6163	Remote Similarity	NPD4244	Approved
0.6163	Remote Similarity	NPD4245	Approved
0.6147	Remote Similarity	NPD6650	Approved
0.6147	Remote Similarity	NPD6649	Approved
0.6117	Remote Similarity	NPD7639	Approved
0.6117	Remote Similarity	NPD7640	Approved
0.6111	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6014	Approved
0.6111	Remote Similarity	NPD6013	Approved
0.6111	Remote Similarity	NPD6012	Approved
0.6105	Remote Similarity	NPD1694	Approved
0.61	Remote Similarity	NPD6001	Approved
0.61	Remote Similarity	NPD7748	Approved
0.6092	Remote Similarity	NPD4758	Discontinued
0.6087	Remote Similarity	NPD6921	Approved
0.6082	Remote Similarity	NPD6903	Approved
0.6068	Remote Similarity	NPD7492	Approved
0.6055	Remote Similarity	NPD7290	Approved
0.6055	Remote Similarity	NPD6883	Approved
0.6055	Remote Similarity	NPD7102	Approved
0.6044	Remote Similarity	NPD3671	Phase 1
0.6042	Remote Similarity	NPD7334	Approved
0.6042	Remote Similarity	NPD6409	Approved
0.6042	Remote Similarity	NPD5330	Approved
0.6042	Remote Similarity	NPD7146	Approved
0.6042	Remote Similarity	NPD6684	Approved
0.6042	Remote Similarity	NPD7521	Approved
0.6018	Remote Similarity	NPD6009	Approved
0.6018	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD6054	Approved
0.5977	Remote Similarity	NPD4789	Approved
0.5977	Remote Similarity	NPD2686	Approved
0.5977	Remote Similarity	NPD2254	Approved
0.5977	Remote Similarity	NPD2687	Approved
0.5966	Remote Similarity	NPD7078	Approved
0.5966	Remote Similarity	NPD8293	Discontinued
0.5962	Remote Similarity	NPD8418	Phase 2
0.5957	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD5983	Phase 2
0.5948	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6016	Approved
0.5948	Remote Similarity	NPD6015	Approved
0.5946	Remote Similarity	NPD6882	Approved
0.5946	Remote Similarity	NPD8297	Approved
0.5922	Remote Similarity	NPD4755	Approved
0.5918	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5737	Approved
0.5918	Remote Similarity	NPD6672	Approved
0.5917	Remote Similarity	NPD7736	Approved
0.59	Remote Similarity	NPD7515	Phase 2
0.5897	Remote Similarity	NPD6370	Approved
0.5897	Remote Similarity	NPD5988	Approved
0.5893	Remote Similarity	NPD8133	Approved
0.5888	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7507	Approved
0.5876	Remote Similarity	NPD3618	Phase 1
0.587	Remote Similarity	NPD4802	Phase 2
0.587	Remote Similarity	NPD4238	Approved
0.587	Remote Similarity	NPD5364	Discontinued
0.5862	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD3726	Approved
0.5862	Remote Similarity	NPD3725	Approved
0.5859	Remote Similarity	NPD5328	Approved
0.5847	Remote Similarity	NPD7604	Phase 2
0.5825	Remote Similarity	NPD4697	Phase 3
0.581	Remote Similarity	NPD4696	Approved
0.581	Remote Similarity	NPD5285	Approved
0.581	Remote Similarity	NPD4700	Approved
0.581	Remote Similarity	NPD5286	Approved
0.58	Remote Similarity	NPD5207	Approved
0.5789	Remote Similarity	NPD6274	Approved
0.5755	Remote Similarity	NPD5223	Approved
0.575	Remote Similarity	NPD6336	Discontinued
0.5743	Remote Similarity	NPD6079	Approved
0.5739	Remote Similarity	NPD6317	Approved
0.5738	Remote Similarity	NPD7319	Approved
0.5714	Remote Similarity	NPD4225	Approved
0.5714	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD8328	Phase 3
0.5714	Remote Similarity	NPD6098	Approved
0.5701	Remote Similarity	NPD5224	Approved
0.5701	Remote Similarity	NPD4633	Approved
0.5701	Remote Similarity	NPD5225	Approved
0.5701	Remote Similarity	NPD5211	Phase 2
0.5701	Remote Similarity	NPD5226	Approved
0.57	Remote Similarity	NPD6080	Approved
0.57	Remote Similarity	NPD6673	Approved
0.57	Remote Similarity	NPD6904	Approved
0.5696	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD615	Clinical (unspecified phase)
0.569	Remote Similarity	NPD6313	Approved
0.569	Remote Similarity	NPD6314	Approved
0.569	Remote Similarity	NPD6335	Approved
0.5686	Remote Similarity	NPD4202	Approved
0.5686	Remote Similarity	NPD8171	Discontinued
0.5673	Remote Similarity	NPD5221	Approved
0.5673	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5222	Approved
0.567	Remote Similarity	NPD3668	Phase 3
0.5656	Remote Similarity	NPD6033	Approved
0.5652	Remote Similarity	NPD6940	Discontinued
0.5648	Remote Similarity	NPD4754	Approved
0.5648	Remote Similarity	NPD5174	Approved
0.5648	Remote Similarity	NPD5175	Approved
0.5647	Remote Similarity	NPD371	Approved
0.5647	Remote Similarity	NPD7909	Approved
0.5641	Remote Similarity	NPD7101	Approved
0.5641	Remote Similarity	NPD7100	Approved
0.5631	Remote Similarity	NPD5282	Discontinued
0.5625	Remote Similarity	NPD3667	Approved
0.5625	Remote Similarity	NPD4634	Approved
0.5619	Remote Similarity	NPD6084	Phase 2
0.5619	Remote Similarity	NPD5173	Approved
0.5619	Remote Similarity	NPD6083	Phase 2
0.5618	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD1811	Approved
0.5604	Remote Similarity	NPD1810	Approved
0.56	Remote Similarity	NPD5208	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