NPASS Compound

Structure

CID31349 OpenBabel06191715362D 25 27 0 0 1 0 0 0 0 0999 V2000 -3.6808 -3.4345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2026 0.8578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -1.4945 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 -5.1808 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -2.5685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6808 -1.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1808 -0.8364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 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 -0.0000 -2.0000 0.0000 C 0 0 1 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 -5.1808 -2.5685 0.0000 C 0 0 0 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 -3.5116 -0.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6808 -3.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.6499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6808 -1.7024 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 10 1 0 0 0 0 4 17 1 0 0 0 0 5 8 1 0 0 0 0 5 23 1 0 0 0 0 6 1 1 1 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 3 1 6 0 0 0 7 8 1 0 0 0 0 8 16 1 6 0 0 0 9 4 1 6 0 0 0 9 11 1 0 0 0 0 9 24 1 0 0 0 0 10 16 1 1 0 0 0 10 25 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 1 0 0 0 12 13 1 0 0 0 0 12 19 1 6 0 0 0 13 15 1 0 0 0 0 13 20 1 1 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 25 1 6 0 0 0 16 2 1 1 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.16
Volume:	336.098
LogP:	-0.399
LogD:	-0.642
LogS:	-1.192
# Rotatable Bonds:	3
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.351
Synthetic Accessibility Score:	4.762
Fsp3:	0.938
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:	-5.68
MDCK Permeability:	0.0001292416563956067
Pgp-inhibitor:	0.316
Pgp-substrate:	0.895
Human Intestinal Absorption (HIA):	0.9
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	20.31947135925293%
Volume Distribution (VD):	0.384
Pgp-substrate:	73.05677795410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.587
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	1.819
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.197
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.213
Carcinogencity:	0.088
Eye Corrosion:	0.004
Eye Irritation:	0.049
Respiratory Toxicity:	0.633

Download Data

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

Natural Product: NPC31349

Natural Product ID:	NPC31349
*Common Name:**	Patriscabroside I
IUPAC Name:	(4R,4aS,6S,7S,7aR)-7-hydroxy-4,7-dimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4,4a,5,6,7a-hexahydrocyclopenta[c]pyran-3-one
Synonyms:	Patriscabroside I
Standard InCHIKey:	ZHEBCILICLSWEG-XBNYBDERSA-N
Standard InCHI:	InChI=1S/C16H26O9/c1-6-7-3-10(16(2,22)8(7)5-23-14(6)21)25-15-13(20)12(19)11(18)9(4-17)24-15/h6-13,15,17-20,22H,3-5H2,1-2H3/t6-,7-,8+,9-,10+,11-,12+,13-,15+,16+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2C[C@H]3[C@@H]([C@]2(C)O)COC(=O)[C@@H]3C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152456
PubChem CID:	71453062
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23002924]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29799195]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[463286]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[463286]

☑ 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 NPC31349 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	384
0.1-0.2	3205
0.2-0.3	9310
0.3-0.4	13105
0.4-0.5	6922
0.5-0.6	6276
0.6-0.7	3114
0.7-0.8	367
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC470657
0.8765	High Similarity	NPC83108
0.8765	High Similarity	NPC214030
0.8642	High Similarity	NPC279575
0.8537	High Similarity	NPC70996
0.837	Intermediate Similarity	NPC215570
0.8333	Intermediate Similarity	NPC170595
0.8315	Intermediate Similarity	NPC470009
0.8272	Intermediate Similarity	NPC470659
0.8272	Intermediate Similarity	NPC470660
0.8144	Intermediate Similarity	NPC37240
0.8125	Intermediate Similarity	NPC3488
0.8125	Intermediate Similarity	NPC287539
0.8043	Intermediate Similarity	NPC235051
0.8041	Intermediate Similarity	NPC4899
0.8041	Intermediate Similarity	NPC177013
0.8041	Intermediate Similarity	NPC35185
0.8041	Intermediate Similarity	NPC474730
0.8	Intermediate Similarity	NPC314364
0.8	Intermediate Similarity	NPC472273
0.798	Intermediate Similarity	NPC127235
0.798	Intermediate Similarity	NPC170432
0.7955	Intermediate Similarity	NPC474266
0.7901	Intermediate Similarity	NPC98711
0.7901	Intermediate Similarity	NPC475062
0.79	Intermediate Similarity	NPC148270
0.79	Intermediate Similarity	NPC197813
0.79	Intermediate Similarity	NPC80338
0.7882	Intermediate Similarity	NPC474003
0.7857	Intermediate Similarity	NPC292803
0.7843	Intermediate Similarity	NPC193741
0.7841	Intermediate Similarity	NPC475849
0.7822	Intermediate Similarity	NPC110701
0.7812	Intermediate Similarity	NPC261372
0.7812	Intermediate Similarity	NPC58267
0.7812	Intermediate Similarity	NPC263674
0.7778	Intermediate Similarity	NPC471253
0.7778	Intermediate Similarity	NPC475928
0.7767	Intermediate Similarity	NPC469824
0.7727	Intermediate Similarity	NPC216941
0.7723	Intermediate Similarity	NPC203974
0.7711	Intermediate Similarity	NPC184550
0.7711	Intermediate Similarity	NPC185419
0.77	Intermediate Similarity	NPC132304
0.77	Intermediate Similarity	NPC123070
0.77	Intermediate Similarity	NPC88890
0.77	Intermediate Similarity	NPC114365
0.77	Intermediate Similarity	NPC470167
0.77	Intermediate Similarity	NPC154962
0.77	Intermediate Similarity	NPC18044
0.77	Intermediate Similarity	NPC169089
0.77	Intermediate Similarity	NPC177518
0.77	Intermediate Similarity	NPC18433
0.7692	Intermediate Similarity	NPC475924
0.7692	Intermediate Similarity	NPC477489
0.7692	Intermediate Similarity	NPC475851
0.7683	Intermediate Similarity	NPC241265
0.7683	Intermediate Similarity	NPC285003
0.7677	Intermediate Similarity	NPC470172
0.7653	Intermediate Similarity	NPC20028
0.7647	Intermediate Similarity	NPC469826
0.7629	Intermediate Similarity	NPC472290
0.7629	Intermediate Similarity	NPC328180
0.7629	Intermediate Similarity	NPC278028
0.7629	Intermediate Similarity	NPC471241
0.7624	Intermediate Similarity	NPC215408
0.7619	Intermediate Similarity	NPC248427
0.7619	Intermediate Similarity	NPC291228
0.7619	Intermediate Similarity	NPC308096
0.7609	Intermediate Similarity	NPC51662
0.7604	Intermediate Similarity	NPC93869
0.7604	Intermediate Similarity	NPC6765
0.76	Intermediate Similarity	NPC473406
0.76	Intermediate Similarity	NPC107385
0.7576	Intermediate Similarity	NPC477172
0.7576	Intermediate Similarity	NPC478181
0.7576	Intermediate Similarity	NPC67296
0.7573	Intermediate Similarity	NPC227879
0.7573	Intermediate Similarity	NPC208333
0.7573	Intermediate Similarity	NPC236753
0.7573	Intermediate Similarity	NPC228190
0.7561	Intermediate Similarity	NPC50228
0.7561	Intermediate Similarity	NPC97736
0.7547	Intermediate Similarity	NPC79193
0.7526	Intermediate Similarity	NPC161293
0.7526	Intermediate Similarity	NPC474297
0.75	Intermediate Similarity	NPC158302
0.75	Intermediate Similarity	NPC85759
0.75	Intermediate Similarity	NPC477344
0.75	Intermediate Similarity	NPC471254
0.75	Intermediate Similarity	NPC63897
0.75	Intermediate Similarity	NPC22742
0.75	Intermediate Similarity	NPC304163
0.75	Intermediate Similarity	NPC146992
0.75	Intermediate Similarity	NPC274588
0.75	Intermediate Similarity	NPC80191
0.75	Intermediate Similarity	NPC294748
0.75	Intermediate Similarity	NPC477346
0.75	Intermediate Similarity	NPC310031
0.75	Intermediate Similarity	NPC106668
0.7476	Intermediate Similarity	NPC202898
0.7476	Intermediate Similarity	NPC92890
0.7476	Intermediate Similarity	NPC475319
0.7476	Intermediate Similarity	NPC167044
0.7476	Intermediate Similarity	NPC472079
0.7475	Intermediate Similarity	NPC41843
0.747	Intermediate Similarity	NPC211428
0.7451	Intermediate Similarity	NPC166079
0.7449	Intermediate Similarity	NPC236580
0.7449	Intermediate Similarity	NPC304445
0.7449	Intermediate Similarity	NPC210157
0.7439	Intermediate Similarity	NPC206601
0.7426	Intermediate Similarity	NPC27687
0.7426	Intermediate Similarity	NPC34562
0.7412	Intermediate Similarity	NPC163812
0.7412	Intermediate Similarity	NPC206823
0.7407	Intermediate Similarity	NPC179429
0.7404	Intermediate Similarity	NPC233433
0.7404	Intermediate Similarity	NPC220836
0.7404	Intermediate Similarity	NPC92297
0.7404	Intermediate Similarity	NPC94086
0.7404	Intermediate Similarity	NPC473817
0.7404	Intermediate Similarity	NPC273002
0.74	Intermediate Similarity	NPC298266
0.74	Intermediate Similarity	NPC178853
0.74	Intermediate Similarity	NPC476839
0.74	Intermediate Similarity	NPC476838
0.74	Intermediate Similarity	NPC259654
0.7379	Intermediate Similarity	NPC176756
0.7374	Intermediate Similarity	NPC37866
0.7368	Intermediate Similarity	NPC246173
0.7358	Intermediate Similarity	NPC477492
0.7353	Intermediate Similarity	NPC469827
0.7353	Intermediate Similarity	NPC100078
0.7353	Intermediate Similarity	NPC88469
0.7347	Intermediate Similarity	NPC170527
0.7347	Intermediate Similarity	NPC296936
0.734	Intermediate Similarity	NPC33398
0.7333	Intermediate Similarity	NPC123204
0.7333	Intermediate Similarity	NPC184915
0.7333	Intermediate Similarity	NPC307400
0.7333	Intermediate Similarity	NPC290012
0.7333	Intermediate Similarity	NPC182185
0.7333	Intermediate Similarity	NPC238056
0.7333	Intermediate Similarity	NPC472204
0.7333	Intermediate Similarity	NPC476087
0.7333	Intermediate Similarity	NPC475667
0.7333	Intermediate Similarity	NPC475327
0.7333	Intermediate Similarity	NPC477331
0.7333	Intermediate Similarity	NPC269318
0.7333	Intermediate Similarity	NPC169345
0.7333	Intermediate Similarity	NPC224953
0.7333	Intermediate Similarity	NPC143421
0.7333	Intermediate Similarity	NPC173328
0.7333	Intermediate Similarity	NPC259294
0.7333	Intermediate Similarity	NPC126685
0.7333	Intermediate Similarity	NPC183888
0.7333	Intermediate Similarity	NPC472201
0.7333	Intermediate Similarity	NPC472205
0.7333	Intermediate Similarity	NPC119583
0.7333	Intermediate Similarity	NPC89843
0.7333	Intermediate Similarity	NPC297768
0.7333	Intermediate Similarity	NPC477318
0.7333	Intermediate Similarity	NPC106760
0.7333	Intermediate Similarity	NPC27289
0.7333	Intermediate Similarity	NPC477347
0.7333	Intermediate Similarity	NPC44782
0.7333	Intermediate Similarity	NPC477317
0.7333	Intermediate Similarity	NPC472202
0.7333	Intermediate Similarity	NPC472203
0.7333	Intermediate Similarity	NPC475270
0.7333	Intermediate Similarity	NPC186992
0.7333	Intermediate Similarity	NPC477319
0.7333	Intermediate Similarity	NPC472200
0.7333	Intermediate Similarity	NPC115013
0.7327	Intermediate Similarity	NPC244969
0.7327	Intermediate Similarity	NPC94919
0.7327	Intermediate Similarity	NPC310138
0.7327	Intermediate Similarity	NPC134967
0.7327	Intermediate Similarity	NPC114700
0.7327	Intermediate Similarity	NPC470029
0.7327	Intermediate Similarity	NPC213528
0.7327	Intermediate Similarity	NPC80144
0.732	Intermediate Similarity	NPC470423
0.7292	Intermediate Similarity	NPC274274
0.7292	Intermediate Similarity	NPC294643
0.7292	Intermediate Similarity	NPC473150
0.7283	Intermediate Similarity	NPC474156
0.7282	Intermediate Similarity	NPC306776
0.7273	Intermediate Similarity	NPC188793
0.7273	Intermediate Similarity	NPC470591
0.7264	Intermediate Similarity	NPC473062
0.7263	Intermediate Similarity	NPC50464
0.7263	Intermediate Similarity	NPC93190
0.7253	Intermediate Similarity	NPC212340
0.7245	Intermediate Similarity	NPC470191
0.7245	Intermediate Similarity	NPC57964
0.7245	Intermediate Similarity	NPC94582
0.7238	Intermediate Similarity	NPC469825
0.7238	Intermediate Similarity	NPC217041

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 NPC31349 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	421
0.1-0.2	3533
0.2-0.3	3475
0.3-0.4	911
0.4-0.5	395
0.5-0.6	284
0.6-0.7	124
0.7-0.8	7
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
0.77	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD8138	Approved
0.7157	Intermediate Similarity	NPD8082	Approved
0.7157	Intermediate Similarity	NPD8086	Approved
0.7157	Intermediate Similarity	NPD8085	Approved
0.7157	Intermediate Similarity	NPD8139	Approved
0.7157	Intermediate Similarity	NPD8083	Approved
0.7157	Intermediate Similarity	NPD8084	Approved
0.7087	Intermediate Similarity	NPD8275	Approved
0.7087	Intermediate Similarity	NPD8276	Approved
0.7019	Intermediate Similarity	NPD8081	Approved
0.7	Intermediate Similarity	NPD4802	Phase 2
0.7	Intermediate Similarity	NPD4238	Approved
0.6989	Remote Similarity	NPD3669	Approved
0.6989	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD8133	Approved
0.6957	Remote Similarity	NPD1780	Approved
0.6957	Remote Similarity	NPD1779	Approved
0.6952	Remote Similarity	NPD8393	Approved
0.6887	Remote Similarity	NPD8140	Approved
0.6887	Remote Similarity	NPD8307	Discontinued
0.6869	Remote Similarity	NPD8171	Discontinued
0.6854	Remote Similarity	NPD3702	Approved
0.6759	Remote Similarity	NPD8305	Approved
0.6759	Remote Similarity	NPD8306	Approved
0.6752	Remote Similarity	NPD7507	Approved
0.6729	Remote Similarity	NPD6412	Phase 2
0.6697	Remote Similarity	NPD8087	Discontinued
0.6628	Remote Similarity	NPD898	Approved
0.6628	Remote Similarity	NPD896	Approved
0.6628	Remote Similarity	NPD897	Approved
0.6585	Remote Similarity	NPD3198	Approved
0.6583	Remote Similarity	NPD7319	Approved
0.6559	Remote Similarity	NPD7329	Approved
0.6514	Remote Similarity	NPD6686	Approved
0.6491	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7909	Approved
0.6444	Remote Similarity	NPD3181	Approved
0.6417	Remote Similarity	NPD8293	Discontinued
0.6415	Remote Similarity	NPD1700	Approved
0.6404	Remote Similarity	NPD6940	Discontinued
0.6404	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD1811	Approved
0.6374	Remote Similarity	NPD1810	Approved
0.6364	Remote Similarity	NPD7736	Approved
0.6356	Remote Similarity	NPD6370	Approved
0.6355	Remote Similarity	NPD8300	Approved
0.6355	Remote Similarity	NPD8301	Approved
0.6354	Remote Similarity	NPD6435	Approved
0.6348	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6319	Approved
0.6306	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6118	Approved
0.6277	Remote Similarity	NPD6114	Approved
0.6277	Remote Similarity	NPD6697	Approved
0.6277	Remote Similarity	NPD6115	Approved
0.6271	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD8513	Phase 3
0.6271	Remote Similarity	NPD8517	Approved
0.6271	Remote Similarity	NPD8515	Approved
0.6271	Remote Similarity	NPD8516	Approved
0.625	Remote Similarity	NPD7492	Approved
0.6218	Remote Similarity	NPD8080	Discontinued
0.6207	Remote Similarity	NPD6009	Approved
0.6198	Remote Similarity	NPD6616	Approved
0.6195	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD8345	Approved
0.6186	Remote Similarity	NPD6059	Approved
0.6186	Remote Similarity	NPD8347	Approved
0.6186	Remote Similarity	NPD8377	Approved
0.6186	Remote Similarity	NPD6054	Approved
0.6186	Remote Similarity	NPD8294	Approved
0.6186	Remote Similarity	NPD8346	Approved
0.617	Remote Similarity	NPD6116	Phase 1
0.6154	Remote Similarity	NPD7327	Approved
0.6154	Remote Similarity	NPD7328	Approved
0.6148	Remote Similarity	NPD7078	Approved
0.6146	Remote Similarity	NPD5368	Approved
0.6146	Remote Similarity	NPD6928	Phase 2
0.614	Remote Similarity	NPD6882	Approved
0.6134	Remote Similarity	NPD6015	Approved
0.6134	Remote Similarity	NPD8033	Approved
0.6134	Remote Similarity	NPD8378	Approved
0.6134	Remote Similarity	NPD6016	Approved
0.6134	Remote Similarity	NPD8296	Approved
0.6134	Remote Similarity	NPD8380	Approved
0.6134	Remote Similarity	NPD8335	Approved
0.6134	Remote Similarity	NPD8379	Approved
0.6102	Remote Similarity	NPD7516	Approved
0.6087	Remote Similarity	NPD4632	Approved
0.6083	Remote Similarity	NPD5988	Approved
0.6064	Remote Similarity	NPD6117	Approved
0.6049	Remote Similarity	NPD893	Approved
0.6049	Remote Similarity	NPD892	Phase 3
0.6049	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD888	Phase 3
0.6049	Remote Similarity	NPD891	Phase 3
0.6044	Remote Similarity	NPD2687	Approved
0.6044	Remote Similarity	NPD2254	Approved
0.6044	Remote Similarity	NPD2686	Approved
0.6033	Remote Similarity	NPD8328	Phase 3
0.6022	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD46	Approved
0.6019	Remote Similarity	NPD6698	Approved
0.6	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD8297	Approved
0.5984	Remote Similarity	NPD8342	Approved
0.5984	Remote Similarity	NPD8341	Approved
0.5984	Remote Similarity	NPD8299	Approved
0.5984	Remote Similarity	NPD8340	Approved
0.5978	Remote Similarity	NPD5777	Approved
0.5977	Remote Similarity	NPD8961	Approved
0.5976	Remote Similarity	NPD3730	Approved
0.5976	Remote Similarity	NPD3728	Approved
0.5962	Remote Similarity	NPD7983	Approved
0.5957	Remote Similarity	NPD3703	Phase 2
0.5935	Remote Similarity	NPD8451	Approved
0.5934	Remote Similarity	NPD3698	Phase 2
0.5929	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD371	Approved
0.5893	Remote Similarity	NPD7128	Approved
0.5893	Remote Similarity	NPD6675	Approved
0.5893	Remote Similarity	NPD5739	Approved
0.5893	Remote Similarity	NPD6402	Approved
0.5887	Remote Similarity	NPD8448	Approved
0.5877	Remote Similarity	NPD6372	Approved
0.5877	Remote Similarity	NPD6373	Approved
0.587	Remote Similarity	NPD4245	Approved
0.587	Remote Similarity	NPD4244	Approved
0.5854	Remote Similarity	NPD894	Approved
0.5854	Remote Similarity	NPD889	Approved
0.5854	Remote Similarity	NPD887	Approved
0.5854	Remote Similarity	NPD895	Approved
0.5843	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5701	Approved
0.5841	Remote Similarity	NPD5697	Approved
0.5841	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2267	Suspended
0.5802	Remote Similarity	NPD905	Approved
0.5802	Remote Similarity	NPD904	Phase 3
0.5789	Remote Similarity	NPD7320	Approved
0.5789	Remote Similarity	NPD6881	Approved
0.5789	Remote Similarity	NPD6899	Approved
0.5784	Remote Similarity	NPD4249	Approved
0.578	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6650	Approved
0.5776	Remote Similarity	NPD6649	Approved
0.5772	Remote Similarity	NPD7829	Approved
0.5772	Remote Similarity	NPD7830	Approved
0.576	Remote Similarity	NPD8074	Phase 3
0.5758	Remote Similarity	NPD5369	Approved
0.575	Remote Similarity	NPD7641	Discontinued
0.5748	Remote Similarity	NPD8391	Approved
0.5748	Remote Similarity	NPD8392	Approved
0.5748	Remote Similarity	NPD8390	Approved
0.5747	Remote Similarity	NPD6123	Approved
0.5739	Remote Similarity	NPD6012	Approved
0.5739	Remote Similarity	NPD6013	Approved
0.5739	Remote Similarity	NPD6014	Approved
0.5738	Remote Similarity	NPD5983	Phase 2
0.5732	Remote Similarity	NPD2269	Approved
0.5728	Remote Similarity	NPD4251	Approved
0.5728	Remote Similarity	NPD4250	Approved
0.5714	Remote Similarity	NPD8336	Approved
0.5714	Remote Similarity	NPD6033	Approved
0.5714	Remote Similarity	NPD8337	Approved
0.569	Remote Similarity	NPD4634	Approved
0.569	Remote Similarity	NPD6371	Approved
0.569	Remote Similarity	NPD6883	Approved
0.569	Remote Similarity	NPD7102	Approved
0.569	Remote Similarity	NPD7290	Approved
0.5688	Remote Similarity	NPD6083	Phase 2
0.5688	Remote Similarity	NPD6084	Phase 2
0.5657	Remote Similarity	NPD4819	Approved
0.5657	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4822	Approved
0.5657	Remote Similarity	NPD4821	Approved
0.5657	Remote Similarity	NPD4820	Approved
0.5652	Remote Similarity	NPD6011	Approved
0.5648	Remote Similarity	NPD5695	Phase 3
0.5645	Remote Similarity	NPD6067	Discontinued
0.5645	Remote Similarity	NPD7642	Approved
0.5645	Remote Similarity	NPD7604	Phase 2
0.5644	Remote Similarity	NPD5362	Discontinued
0.5641	Remote Similarity	NPD6869	Approved
0.5641	Remote Similarity	NPD6617	Approved
0.5641	Remote Similarity	NPD6847	Approved
0.5641	Remote Similarity	NPD8130	Phase 1
0.5638	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6081	Approved
0.5631	Remote Similarity	NPD5786	Approved
0.5625	Remote Similarity	NPD2257	Approved
0.5619	Remote Similarity	NPD6101	Approved
0.5619	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6008	Approved
0.561	Remote Similarity	NPD8444	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