NPASS Compound

Structure

NPC470657 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 -4.9651 1.8601 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 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 0.1910 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 -2.1119 2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0140 2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3198 1.8090 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 1.7321 0.0000 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 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8061 3.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 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 1.7321 -2.0000 0.0000 O 0 0 0 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5493 3.8164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8551 3.4563 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 3 4 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 9 1 0 0 0 0 6 22 1 0 0 0 0 7 1 1 1 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 3 1 6 0 0 0 8 9 1 0 0 0 0 9 16 1 6 0 0 0 10 5 1 1 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 6 0 0 0 12 13 1 0 0 0 0 12 19 1 1 0 0 0 13 15 1 0 0 0 0 13 20 1 6 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 15 24 1 1 0 0 0 16 2 1 1 0 0 0 16 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.16
Volume:	327.308
LogP:	0.096
LogD:	0.061
LogS:	-1.409
# Rotatable Bonds:	3
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.469
Synthetic Accessibility Score:	4.684
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:	-5.501
MDCK Permeability:	0.00015351423644460738
Pgp-inhibitor:	0.013
Pgp-substrate:	0.474
Human Intestinal Absorption (HIA):	0.736
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.786

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.149
Plasma Protein Binding (PPB):	28.155616760253906%
Volume Distribution (VD):	0.546
Pgp-substrate:	55.39500045776367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.668
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.73
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	2.281
Half-life (T1/2):	0.733

ADMET: Toxicity

hERG Blockers:	0.269
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.225
Carcinogencity:	0.138
Eye Corrosion:	0.004
Eye Irritation:	0.081
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC470657

Natural Product ID:	NPC470657
*Common Name:**	Patriridoside E
IUPAC Name:	(4R,4aS,7R,7aR)-4,7-dimethyl-7-[(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:	Patriridoside E
Standard InCHIKey:	HKMDHBXRMZEVHY-CFWSZCEDSA-N
Standard InCHI:	InChI=1S/C16H26O8/c1-7-8-3-4-16(2,9(8)6-22-14(7)21)24-15-13(20)12(19)11(18)10(5-17)23-15/h7-13,15,17-20H,3-6H2,1-2H3/t7-,8-,9+,10-,11-,12+,13-,15+,16-/m1/s1
SMILES:	CC1C2CCC(C2COC1=O)(C)OC3C(C(C(C(O3)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152443
PubChem CID:	71453061
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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]
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[544219]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[544219]

☑ 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 NPC470657 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	377
0.1-0.2	3149
0.2-0.3	9077
0.3-0.4	13166
0.4-0.5	6909
0.5-0.6	6226
0.6-0.7	3344
0.7-0.8	433
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC31349
0.8642	High Similarity	NPC214030
0.8642	High Similarity	NPC83108
0.8642	High Similarity	NPC70996
0.8519	High Similarity	NPC279575
0.8462	Intermediate Similarity	NPC215570
0.8409	Intermediate Similarity	NPC470009
0.8229	Intermediate Similarity	NPC37240
0.8214	Intermediate Similarity	NPC170595
0.8211	Intermediate Similarity	NPC287539
0.8211	Intermediate Similarity	NPC3488
0.8148	Intermediate Similarity	NPC470660
0.8148	Intermediate Similarity	NPC470659
0.8125	Intermediate Similarity	NPC474730
0.8125	Intermediate Similarity	NPC35185
0.8125	Intermediate Similarity	NPC4899
0.8125	Intermediate Similarity	NPC177013
0.809	Intermediate Similarity	NPC314364
0.8085	Intermediate Similarity	NPC472273
0.8061	Intermediate Similarity	NPC127235
0.8046	Intermediate Similarity	NPC474266
0.8	Intermediate Similarity	NPC98711
0.8	Intermediate Similarity	NPC475062
0.798	Intermediate Similarity	NPC148270
0.798	Intermediate Similarity	NPC80338
0.798	Intermediate Similarity	NPC197813
0.7976	Intermediate Similarity	NPC474003
0.7935	Intermediate Similarity	NPC235051
0.7931	Intermediate Similarity	NPC475849
0.7895	Intermediate Similarity	NPC263674
0.7895	Intermediate Similarity	NPC261372
0.7895	Intermediate Similarity	NPC58267
0.7879	Intermediate Similarity	NPC170432
0.7857	Intermediate Similarity	NPC475928
0.7857	Intermediate Similarity	NPC471253
0.7843	Intermediate Similarity	NPC469824
0.7816	Intermediate Similarity	NPC216941
0.7805	Intermediate Similarity	NPC184550
0.7805	Intermediate Similarity	NPC185419
0.78	Intermediate Similarity	NPC203974
0.7778	Intermediate Similarity	NPC470167
0.7778	Intermediate Similarity	NPC241265
0.7778	Intermediate Similarity	NPC285003
0.7767	Intermediate Similarity	NPC477489
0.7755	Intermediate Similarity	NPC292803
0.7755	Intermediate Similarity	NPC470172
0.7745	Intermediate Similarity	NPC193741
0.7732	Intermediate Similarity	NPC20028
0.7723	Intermediate Similarity	NPC110701
0.7723	Intermediate Similarity	NPC469826
0.7711	Intermediate Similarity	NPC291228
0.7711	Intermediate Similarity	NPC308096
0.7708	Intermediate Similarity	NPC471241
0.7708	Intermediate Similarity	NPC472290
0.7708	Intermediate Similarity	NPC328180
0.7708	Intermediate Similarity	NPC278028
0.77	Intermediate Similarity	NPC215408
0.7692	Intermediate Similarity	NPC51662
0.7677	Intermediate Similarity	NPC107385
0.7677	Intermediate Similarity	NPC473406
0.7654	Intermediate Similarity	NPC97736
0.7654	Intermediate Similarity	NPC50228
0.7653	Intermediate Similarity	NPC477172
0.7653	Intermediate Similarity	NPC478181
0.7653	Intermediate Similarity	NPC67296
0.7647	Intermediate Similarity	NPC227879
0.7647	Intermediate Similarity	NPC208333
0.7647	Intermediate Similarity	NPC236753
0.7647	Intermediate Similarity	NPC228190
0.7619	Intermediate Similarity	NPC79193
0.7604	Intermediate Similarity	NPC474297
0.7604	Intermediate Similarity	NPC161293
0.76	Intermediate Similarity	NPC132304
0.76	Intermediate Similarity	NPC169089
0.76	Intermediate Similarity	NPC88890
0.76	Intermediate Similarity	NPC114365
0.76	Intermediate Similarity	NPC177518
0.76	Intermediate Similarity	NPC154962
0.76	Intermediate Similarity	NPC18044
0.76	Intermediate Similarity	NPC123070
0.76	Intermediate Similarity	NPC18433
0.7596	Intermediate Similarity	NPC475924
0.7596	Intermediate Similarity	NPC475851
0.7586	Intermediate Similarity	NPC146992
0.7586	Intermediate Similarity	NPC22742
0.7586	Intermediate Similarity	NPC158302
0.7586	Intermediate Similarity	NPC85759
0.7586	Intermediate Similarity	NPC294748
0.7586	Intermediate Similarity	NPC477346
0.7586	Intermediate Similarity	NPC477344
0.7579	Intermediate Similarity	NPC63897
0.7576	Intermediate Similarity	NPC310031
0.7576	Intermediate Similarity	NPC304163
0.7576	Intermediate Similarity	NPC471254
0.7576	Intermediate Similarity	NPC80191
0.7576	Intermediate Similarity	NPC106668
0.7561	Intermediate Similarity	NPC211428
0.7551	Intermediate Similarity	NPC41843
0.7549	Intermediate Similarity	NPC202898
0.7549	Intermediate Similarity	NPC92890
0.7549	Intermediate Similarity	NPC475319
0.7549	Intermediate Similarity	NPC472079
0.7531	Intermediate Similarity	NPC206601
0.7526	Intermediate Similarity	NPC304445
0.7526	Intermediate Similarity	NPC236580
0.7525	Intermediate Similarity	NPC166079
0.75	Intermediate Similarity	NPC163812
0.75	Intermediate Similarity	NPC27687
0.75	Intermediate Similarity	NPC248427
0.75	Intermediate Similarity	NPC6765
0.75	Intermediate Similarity	NPC206823
0.75	Intermediate Similarity	NPC93869
0.75	Intermediate Similarity	NPC34562
0.7477	Intermediate Similarity	NPC179429
0.7476	Intermediate Similarity	NPC473817
0.7476	Intermediate Similarity	NPC92297
0.7476	Intermediate Similarity	NPC273002
0.7476	Intermediate Similarity	NPC220836
0.7476	Intermediate Similarity	NPC94086
0.7476	Intermediate Similarity	NPC233433
0.7451	Intermediate Similarity	NPC176756
0.7449	Intermediate Similarity	NPC37866
0.7429	Intermediate Similarity	NPC477492
0.7426	Intermediate Similarity	NPC100078
0.7426	Intermediate Similarity	NPC469827
0.7426	Intermediate Similarity	NPC88469
0.7423	Intermediate Similarity	NPC296936
0.7419	Intermediate Similarity	NPC33398
0.7416	Intermediate Similarity	NPC126685
0.7416	Intermediate Similarity	NPC477319
0.7416	Intermediate Similarity	NPC169345
0.7416	Intermediate Similarity	NPC259294
0.7416	Intermediate Similarity	NPC183888
0.7416	Intermediate Similarity	NPC475667
0.7416	Intermediate Similarity	NPC477331
0.7416	Intermediate Similarity	NPC472205
0.7416	Intermediate Similarity	NPC119583
0.7416	Intermediate Similarity	NPC472203
0.7416	Intermediate Similarity	NPC173328
0.7416	Intermediate Similarity	NPC472201
0.7416	Intermediate Similarity	NPC224953
0.7416	Intermediate Similarity	NPC143421
0.7416	Intermediate Similarity	NPC477318
0.7416	Intermediate Similarity	NPC475327
0.7416	Intermediate Similarity	NPC477347
0.7416	Intermediate Similarity	NPC89843
0.7416	Intermediate Similarity	NPC472202
0.7416	Intermediate Similarity	NPC27289
0.7416	Intermediate Similarity	NPC472200
0.7416	Intermediate Similarity	NPC44782
0.7416	Intermediate Similarity	NPC123204
0.7416	Intermediate Similarity	NPC475270
0.7416	Intermediate Similarity	NPC290012
0.7416	Intermediate Similarity	NPC477317
0.7416	Intermediate Similarity	NPC186992
0.7416	Intermediate Similarity	NPC115013
0.7416	Intermediate Similarity	NPC472204
0.7416	Intermediate Similarity	NPC297768
0.7416	Intermediate Similarity	NPC307400
0.7416	Intermediate Similarity	NPC238056
0.7416	Intermediate Similarity	NPC476087
0.7416	Intermediate Similarity	NPC269318
0.7416	Intermediate Similarity	NPC184915
0.7404	Intermediate Similarity	NPC106760
0.74	Intermediate Similarity	NPC244969
0.74	Intermediate Similarity	NPC80144
0.74	Intermediate Similarity	NPC94919
0.74	Intermediate Similarity	NPC213528
0.7396	Intermediate Similarity	NPC274588
0.7396	Intermediate Similarity	NPC470423
0.7379	Intermediate Similarity	NPC167044
0.7363	Intermediate Similarity	NPC474156
0.7356	Intermediate Similarity	NPC188793
0.7353	Intermediate Similarity	NPC306776
0.7347	Intermediate Similarity	NPC470591
0.7347	Intermediate Similarity	NPC210157
0.734	Intermediate Similarity	NPC93190
0.734	Intermediate Similarity	NPC50464
0.7333	Intermediate Similarity	NPC473062
0.732	Intermediate Similarity	NPC57964
0.732	Intermediate Similarity	NPC94582
0.7317	Intermediate Similarity	NPC477761
0.7317	Intermediate Similarity	NPC477759
0.7317	Intermediate Similarity	NPC286842
0.7317	Intermediate Similarity	NPC477758
0.7317	Intermediate Similarity	NPC477760
0.7317	Intermediate Similarity	NPC477754
0.7312	Intermediate Similarity	NPC472396
0.7308	Intermediate Similarity	NPC118225
0.7308	Intermediate Similarity	NPC217041
0.7308	Intermediate Similarity	NPC469825
0.7303	Intermediate Similarity	NPC267592
0.7303	Intermediate Similarity	NPC60568
0.73	Intermediate Similarity	NPC298266
0.73	Intermediate Similarity	NPC475574
0.73	Intermediate Similarity	NPC108227
0.73	Intermediate Similarity	NPC476839
0.73	Intermediate Similarity	NPC472081
0.73	Intermediate Similarity	NPC178853
0.73	Intermediate Similarity	NPC476838

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 NPC470657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	412
0.1-0.2	3494
0.2-0.3	3479
0.3-0.4	930
0.4-0.5	408
0.5-0.6	276
0.6-0.7	140
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
0.7778	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8138	Approved
0.7228	Intermediate Similarity	NPD8084	Approved
0.7228	Intermediate Similarity	NPD8139	Approved
0.7228	Intermediate Similarity	NPD8083	Approved
0.7228	Intermediate Similarity	NPD8085	Approved
0.7228	Intermediate Similarity	NPD8086	Approved
0.7228	Intermediate Similarity	NPD8082	Approved
0.7157	Intermediate Similarity	NPD8275	Approved
0.7157	Intermediate Similarity	NPD8276	Approved
0.7087	Intermediate Similarity	NPD8081	Approved
0.7079	Intermediate Similarity	NPD4802	Phase 2
0.7079	Intermediate Similarity	NPD4238	Approved
0.7065	Intermediate Similarity	NPD3669	Approved
0.7065	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8133	Approved
0.7033	Intermediate Similarity	NPD1780	Approved
0.7033	Intermediate Similarity	NPD1779	Approved
0.7019	Intermediate Similarity	NPD8393	Approved
0.6952	Remote Similarity	NPD8140	Approved
0.6952	Remote Similarity	NPD8307	Discontinued
0.6939	Remote Similarity	NPD8171	Discontinued
0.6932	Remote Similarity	NPD3702	Approved
0.6822	Remote Similarity	NPD8305	Approved
0.6822	Remote Similarity	NPD8306	Approved
0.681	Remote Similarity	NPD7507	Approved
0.6792	Remote Similarity	NPD6412	Phase 2
0.6759	Remote Similarity	NPD8087	Discontinued
0.6706	Remote Similarity	NPD898	Approved
0.6706	Remote Similarity	NPD896	Approved
0.6706	Remote Similarity	NPD897	Approved
0.6667	Remote Similarity	NPD3198	Approved
0.6639	Remote Similarity	NPD7319	Approved
0.663	Remote Similarity	NPD7329	Approved
0.6574	Remote Similarity	NPD6686	Approved
0.6549	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7909	Approved
0.6517	Remote Similarity	NPD3181	Approved
0.6477	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD1700	Approved
0.646	Remote Similarity	NPD6940	Discontinued
0.6444	Remote Similarity	NPD1810	Approved
0.6444	Remote Similarity	NPD1811	Approved
0.6421	Remote Similarity	NPD6435	Approved
0.6415	Remote Similarity	NPD8300	Approved
0.6415	Remote Similarity	NPD8301	Approved
0.6404	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6114	Approved
0.6344	Remote Similarity	NPD6697	Approved
0.6344	Remote Similarity	NPD6115	Approved
0.6344	Remote Similarity	NPD6118	Approved
0.6333	Remote Similarity	NPD8293	Discontinued
0.6325	Remote Similarity	NPD8516	Approved
0.6325	Remote Similarity	NPD8517	Approved
0.6325	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD8515	Approved
0.6325	Remote Similarity	NPD8513	Phase 3
0.6281	Remote Similarity	NPD7736	Approved
0.6271	Remote Similarity	NPD6370	Approved
0.6271	Remote Similarity	NPD8080	Discontinued
0.6261	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6319	Approved
0.6239	Remote Similarity	NPD8345	Approved
0.6239	Remote Similarity	NPD8347	Approved
0.6239	Remote Similarity	NPD8294	Approved
0.6239	Remote Similarity	NPD8377	Approved
0.6239	Remote Similarity	NPD8346	Approved
0.6237	Remote Similarity	NPD6116	Phase 1
0.6211	Remote Similarity	NPD5368	Approved
0.6211	Remote Similarity	NPD6928	Phase 2
0.6207	Remote Similarity	NPD7328	Approved
0.6207	Remote Similarity	NPD7327	Approved
0.6195	Remote Similarity	NPD6882	Approved
0.6186	Remote Similarity	NPD8379	Approved
0.6186	Remote Similarity	NPD8296	Approved
0.6186	Remote Similarity	NPD8335	Approved
0.6186	Remote Similarity	NPD8380	Approved
0.6186	Remote Similarity	NPD8033	Approved
0.6186	Remote Similarity	NPD8378	Approved
0.6167	Remote Similarity	NPD7492	Approved
0.6154	Remote Similarity	NPD7516	Approved
0.614	Remote Similarity	NPD4632	Approved
0.6129	Remote Similarity	NPD6117	Approved
0.6125	Remote Similarity	NPD892	Phase 3
0.6125	Remote Similarity	NPD888	Phase 3
0.6125	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD893	Approved
0.6125	Remote Similarity	NPD891	Phase 3
0.6116	Remote Similarity	NPD6616	Approved
0.6111	Remote Similarity	NPD2686	Approved
0.6111	Remote Similarity	NPD2687	Approved
0.6111	Remote Similarity	NPD2254	Approved
0.6102	Remote Similarity	NPD6059	Approved
0.6102	Remote Similarity	NPD6054	Approved
0.6087	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8328	Phase 3
0.6078	Remote Similarity	NPD6698	Approved
0.6078	Remote Similarity	NPD46	Approved
0.6066	Remote Similarity	NPD7078	Approved
0.6053	Remote Similarity	NPD6053	Discontinued
0.6053	Remote Similarity	NPD8297	Approved
0.605	Remote Similarity	NPD7503	Approved
0.605	Remote Similarity	NPD6016	Approved
0.605	Remote Similarity	NPD6015	Approved
0.6049	Remote Similarity	NPD3728	Approved
0.6049	Remote Similarity	NPD3730	Approved
0.6047	Remote Similarity	NPD8961	Approved
0.6044	Remote Similarity	NPD5777	Approved
0.6033	Remote Similarity	NPD8341	Approved
0.6033	Remote Similarity	NPD8299	Approved
0.6033	Remote Similarity	NPD8342	Approved
0.6033	Remote Similarity	NPD8340	Approved
0.6022	Remote Similarity	NPD3703	Phase 2
0.6019	Remote Similarity	NPD7983	Approved
0.6	Remote Similarity	NPD3698	Phase 2
0.6	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD8451	Approved
0.5982	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD371	Approved
0.5946	Remote Similarity	NPD6402	Approved
0.5946	Remote Similarity	NPD6675	Approved
0.5946	Remote Similarity	NPD5739	Approved
0.5946	Remote Similarity	NPD7128	Approved
0.5935	Remote Similarity	NPD8448	Approved
0.5934	Remote Similarity	NPD4245	Approved
0.5934	Remote Similarity	NPD4244	Approved
0.5929	Remote Similarity	NPD6372	Approved
0.5929	Remote Similarity	NPD6373	Approved
0.5926	Remote Similarity	NPD887	Approved
0.5926	Remote Similarity	NPD889	Approved
0.5926	Remote Similarity	NPD894	Approved
0.5926	Remote Similarity	NPD895	Approved
0.5909	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD2267	Suspended
0.5893	Remote Similarity	NPD5701	Approved
0.5893	Remote Similarity	NPD5697	Approved
0.5893	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD904	Phase 3
0.5875	Remote Similarity	NPD905	Approved
0.5842	Remote Similarity	NPD4249	Approved
0.5841	Remote Similarity	NPD6899	Approved
0.5841	Remote Similarity	NPD6881	Approved
0.5841	Remote Similarity	NPD7320	Approved
0.5833	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6650	Approved
0.5826	Remote Similarity	NPD6649	Approved
0.582	Remote Similarity	NPD7829	Approved
0.582	Remote Similarity	NPD7830	Approved
0.5816	Remote Similarity	NPD5369	Approved
0.5814	Remote Similarity	NPD6123	Approved
0.5806	Remote Similarity	NPD8074	Phase 3
0.5802	Remote Similarity	NPD2269	Approved
0.5798	Remote Similarity	NPD7641	Discontinued
0.5794	Remote Similarity	NPD8392	Approved
0.5794	Remote Similarity	NPD8391	Approved
0.5794	Remote Similarity	NPD8390	Approved
0.5789	Remote Similarity	NPD6014	Approved
0.5789	Remote Similarity	NPD6013	Approved
0.5789	Remote Similarity	NPD6012	Approved
0.5785	Remote Similarity	NPD5983	Phase 2
0.5784	Remote Similarity	NPD4251	Approved
0.5784	Remote Similarity	NPD4250	Approved
0.576	Remote Similarity	NPD8336	Approved
0.576	Remote Similarity	NPD8337	Approved
0.5741	Remote Similarity	NPD6084	Phase 2
0.5741	Remote Similarity	NPD6083	Phase 2
0.5739	Remote Similarity	NPD6883	Approved
0.5739	Remote Similarity	NPD7290	Approved
0.5739	Remote Similarity	NPD6371	Approved
0.5739	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4819	Approved
0.5714	Remote Similarity	NPD4822	Approved
0.5714	Remote Similarity	NPD4820	Approved
0.5714	Remote Similarity	NPD4821	Approved
0.5702	Remote Similarity	NPD6011	Approved
0.5701	Remote Similarity	NPD5695	Phase 3
0.57	Remote Similarity	NPD5362	Discontinued
0.5699	Remote Similarity	NPD6081	Approved
0.5699	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7604	Phase 2
0.5691	Remote Similarity	NPD7642	Approved
0.569	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD8130	Phase 1
0.569	Remote Similarity	NPD6847	Approved
0.569	Remote Similarity	NPD6617	Approved
0.5686	Remote Similarity	NPD5786	Approved
0.5684	Remote Similarity	NPD2257	Approved
0.5673	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6101	Approved
0.5667	Remote Similarity	NPD4224	Phase 2
0.5664	Remote Similarity	NPD6008	Approved
0.5663	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.566	Remote Similarity	NPD1447	Phase 3
0.566	Remote Similarity	NPD5779	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