NPASS Compound

Structure

NPC216137 OpenBabel07101718282D 37 39 0 0 1 0 0 0 0 0999 V2000 0.6762 -2.2336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2509 -4.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9094 -1.2096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3182 1.0278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5986 -1.8757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8387 1.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4414 1.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8111 1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2674 -0.9442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4491 -1.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6762 -1.2855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1604 -3.5364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9094 -0.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4972 1.5018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9036 -2.5205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9327 1.7332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2674 -0.2615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4105 -0.6029 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1143 0.0122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6762 0.0798 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7868 -1.3168 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4488 0.1641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9243 0.2110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -0.2615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0850 -0.9442 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1058 -3.4656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7304 0.2125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4972 2.4499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1146 -3.4448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7218 2.6574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7054 0.7534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3736 -2.7531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0884 0.2125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6762 1.0278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9977 -2.2411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2378 1.0884 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 11 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 23 1 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 24 1 0 0 0 0 10 32 1 0 0 0 0 11 25 1 1 0 0 0 12 26 2 0 0 0 0 12 32 1 0 0 0 0 13 27 2 0 0 0 0 13 33 1 0 0 0 0 14 28 2 0 0 0 0 14 34 1 0 0 0 0 15 29 2 0 0 0 0 15 35 1 0 0 0 0 16 30 2 0 0 0 0 16 36 1 0 0 0 0 17 20 1 0 0 0 0 17 33 1 1 0 0 0 18 19 1 1 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 31 2 0 0 0 0 20 24 1 1 0 0 0 20 34 1 0 0 0 0 21 25 1 6 0 0 0 21 35 1 0 0 0 0 22 24 1 1 0 0 0 22 36 1 0 0 0 0 23 37 1 0 0 0 0 24 25 1 6 0 0 0 25 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.21
Volume:	504.951
LogP:	2.116
LogD:	0.966
LogS:	-3.481
# Rotatable Bonds:	11
TPSA:	157.8
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	6.056
Fsp3:	0.76
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:	-5.39
MDCK Permeability:	0.0001374579151161015
Pgp-inhibitor:	0.996
Pgp-substrate:	0.172
Human Intestinal Absorption (HIA):	0.865
20% Bioavailability (F20%):	0.865
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.455
Plasma Protein Binding (PPB):	31.389633178710938%
Volume Distribution (VD):	1.493
Pgp-substrate:	44.97652816772461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.73
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	2.802
Half-life (T1/2):	0.58

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.87
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.278
Carcinogencity:	0.112
Eye Corrosion:	0.684
Eye Irritation:	0.373
Respiratory Toxicity:	0.153

Download Data

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

Natural Product: NPC216137

Natural Product ID:	NPC216137
*Common Name:**	YLPWIVXPAOTLTE-MDUHTVMBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YLPWIVXPAOTLTE-MDUHTVMBSA-N
Standard InCHI:	InChI=1S/C25H34O12/c1-11-9-17(33-13(3)27)20(34-14(4)28)24(10-32-12(2)26)22(36-16(6)30)19(31)18-21(35-15(5)29)25(11,24)37-23(18,7)8/h11,17-18,20-22H,9-10H2,1-8H3/t11-,17+,18-,20+,21-,22-,24+,25-/m1/s1
SMILES:	C[C@@H]1C[C@@H]([C@@H]([C@@]2(COC(=O)C)[C@@H](C(=O)[C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL373139
PubChem CID:	11203290
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974580]

☑ 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
Ki	3
Others	7

Activity Type	# Activity
Cell Line	2
Individual Protein	3
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell Line	NIH3T3	Mus musculus	Ki	=	9826.0	nM	PMID[458377]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[458379]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	9830.0	nM	PMID[458378]
NPT35	Others	n.a.		LogP	=	4.0	n.a.	PMID[458378]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	9772.37	nM	PMID[458378]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Imax	=	100.0	%	PMID[458378]
NPT2	Others	Unspecified		Activity	=	3.1	%	PMID[458379]
NPT2	Others	Unspecified		Activity	=	31.7	%	PMID[458379]
NPT2	Others	Unspecified		Activity	=	72.0	%	PMID[458379]
NPT2	Others	Unspecified		Activity	=	94.8	%	PMID[458379]

☑ 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 NPC216137 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	476
0.1-0.2	3826
0.2-0.3	8093
0.3-0.4	13449
0.4-0.5	7161
0.5-0.6	6396
0.6-0.7	2759
0.7-0.8	499
0.8-0.85	29
0.85-0.9	3
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC477441
0.8989	High Similarity	NPC477433
0.8989	High Similarity	NPC477442
0.8989	High Similarity	NPC477444
0.8876	High Similarity	NPC477440
0.8876	High Similarity	NPC477443
0.8791	High Similarity	NPC474379
0.8736	High Similarity	NPC65133
0.8427	Intermediate Similarity	NPC477445
0.8352	Intermediate Similarity	NPC471221
0.8333	Intermediate Similarity	NPC476717
0.8315	Intermediate Similarity	NPC477434
0.8298	Intermediate Similarity	NPC477495
0.8276	Intermediate Similarity	NPC125366
0.8276	Intermediate Similarity	NPC134227
0.8229	Intermediate Similarity	NPC266417
0.8211	Intermediate Similarity	NPC62407
0.8211	Intermediate Similarity	NPC287354
0.8202	Intermediate Similarity	NPC476721
0.8182	Intermediate Similarity	NPC329490
0.8182	Intermediate Similarity	NPC328639
0.8155	Intermediate Similarity	NPC157476
0.8152	Intermediate Similarity	NPC221993
0.8152	Intermediate Similarity	NPC476435
0.8144	Intermediate Similarity	NPC253995
0.8081	Intermediate Similarity	NPC471254
0.8	Intermediate Similarity	NPC55508
0.798	Intermediate Similarity	NPC298266
0.798	Intermediate Similarity	NPC259654
0.7979	Intermediate Similarity	NPC470114
0.7978	Intermediate Similarity	NPC470154
0.7938	Intermediate Similarity	NPC163685
0.7938	Intermediate Similarity	NPC477264
0.7938	Intermediate Similarity	NPC235109
0.7935	Intermediate Similarity	NPC474215
0.7935	Intermediate Similarity	NPC475729
0.7931	Intermediate Similarity	NPC143250
0.7917	Intermediate Similarity	NPC309127
0.7917	Intermediate Similarity	NPC247877
0.7912	Intermediate Similarity	NPC475689
0.7889	Intermediate Similarity	NPC477447
0.7889	Intermediate Similarity	NPC477446
0.7889	Intermediate Similarity	NPC470155
0.7885	Intermediate Similarity	NPC100908
0.7882	Intermediate Similarity	NPC474755
0.7882	Intermediate Similarity	NPC109510
0.7872	Intermediate Similarity	NPC67653
0.7872	Intermediate Similarity	NPC471459
0.7864	Intermediate Similarity	NPC208461
0.7864	Intermediate Similarity	NPC289702
0.785	Intermediate Similarity	NPC190185
0.785	Intermediate Similarity	NPC16081
0.785	Intermediate Similarity	NPC213084
0.785	Intermediate Similarity	NPC475490
0.785	Intermediate Similarity	NPC173686
0.7835	Intermediate Similarity	NPC82633
0.7835	Intermediate Similarity	NPC17336
0.783	Intermediate Similarity	NPC94509
0.7826	Intermediate Similarity	NPC473350
0.7822	Intermediate Similarity	NPC471253
0.7822	Intermediate Similarity	NPC473406
0.7802	Intermediate Similarity	NPC15091
0.7778	Intermediate Similarity	NPC146432
0.7778	Intermediate Similarity	NPC470778
0.7778	Intermediate Similarity	NPC470156
0.7766	Intermediate Similarity	NPC476379
0.7766	Intermediate Similarity	NPC477614
0.7766	Intermediate Similarity	NPC226491
0.7757	Intermediate Similarity	NPC470116
0.7757	Intermediate Similarity	NPC299849
0.7757	Intermediate Similarity	NPC323821
0.7757	Intermediate Similarity	NPC143268
0.7757	Intermediate Similarity	NPC45218
0.7757	Intermediate Similarity	NPC470115
0.7757	Intermediate Similarity	NPC268238
0.7755	Intermediate Similarity	NPC116683
0.7755	Intermediate Similarity	NPC475765
0.7745	Intermediate Similarity	NPC88469
0.7742	Intermediate Similarity	NPC83242
0.7723	Intermediate Similarity	NPC470172
0.7717	Intermediate Similarity	NPC181871
0.7717	Intermediate Similarity	NPC9060
0.7685	Intermediate Similarity	NPC89929
0.7684	Intermediate Similarity	NPC61688
0.7677	Intermediate Similarity	NPC470632
0.7677	Intermediate Similarity	NPC74466
0.767	Intermediate Similarity	NPC200957
0.767	Intermediate Similarity	NPC138908
0.7664	Intermediate Similarity	NPC33360
0.766	Intermediate Similarity	NPC470920
0.7653	Intermediate Similarity	NPC217329
0.7634	Intermediate Similarity	NPC474572
0.7634	Intermediate Similarity	NPC477205
0.7629	Intermediate Similarity	NPC476189
0.7619	Intermediate Similarity	NPC474242
0.7615	Intermediate Similarity	NPC474654
0.7615	Intermediate Similarity	NPC122033
0.7615	Intermediate Similarity	NPC470854
0.7615	Intermediate Similarity	NPC97908
0.7615	Intermediate Similarity	NPC287343
0.7604	Intermediate Similarity	NPC472146
0.7604	Intermediate Similarity	NPC185529
0.76	Intermediate Similarity	NPC472144
0.7596	Intermediate Similarity	NPC166993
0.7596	Intermediate Similarity	NPC201908
0.7596	Intermediate Similarity	NPC176949
0.7593	Intermediate Similarity	NPC473798
0.7593	Intermediate Similarity	NPC477465
0.7582	Intermediate Similarity	NPC475743
0.7579	Intermediate Similarity	NPC236459
0.7576	Intermediate Similarity	NPC475785
0.7553	Intermediate Similarity	NPC228593
0.7553	Intermediate Similarity	NPC235196
0.7553	Intermediate Similarity	NPC243746
0.7553	Intermediate Similarity	NPC474008
0.7551	Intermediate Similarity	NPC470424
0.7545	Intermediate Similarity	NPC17772
0.7528	Intermediate Similarity	NPC307865
0.7528	Intermediate Similarity	NPC471151
0.7527	Intermediate Similarity	NPC473299
0.7527	Intermediate Similarity	NPC219535
0.7527	Intermediate Similarity	NPC237938
0.7525	Intermediate Similarity	NPC477656
0.7524	Intermediate Similarity	NPC273155
0.7523	Intermediate Similarity	NPC251236
0.7523	Intermediate Similarity	NPC96312
0.7523	Intermediate Similarity	NPC328374
0.7523	Intermediate Similarity	NPC40632
0.7523	Intermediate Similarity	NPC477509
0.75	Intermediate Similarity	NPC472145
0.75	Intermediate Similarity	NPC470779
0.75	Intermediate Similarity	NPC13494
0.75	Intermediate Similarity	NPC477284
0.75	Intermediate Similarity	NPC198539
0.75	Intermediate Similarity	NPC97002
0.75	Intermediate Similarity	NPC200580
0.7477	Intermediate Similarity	NPC470777
0.7476	Intermediate Similarity	NPC99510
0.7476	Intermediate Similarity	NPC122811
0.7474	Intermediate Similarity	NPC263802
0.7474	Intermediate Similarity	NPC239938
0.7455	Intermediate Similarity	NPC470775
0.7455	Intermediate Similarity	NPC176513
0.7453	Intermediate Similarity	NPC204652
0.7453	Intermediate Similarity	NPC16657
0.7451	Intermediate Similarity	NPC98225
0.7449	Intermediate Similarity	NPC472148
0.7449	Intermediate Similarity	NPC228700
0.7449	Intermediate Similarity	NPC472147
0.7447	Intermediate Similarity	NPC476715
0.7429	Intermediate Similarity	NPC203974
0.7426	Intermediate Similarity	NPC17183
0.7426	Intermediate Similarity	NPC474724
0.7423	Intermediate Similarity	NPC88337
0.7423	Intermediate Similarity	NPC475211
0.7419	Intermediate Similarity	NPC227170
0.7416	Intermediate Similarity	NPC474020
0.7416	Intermediate Similarity	NPC471046
0.7404	Intermediate Similarity	NPC65523
0.7404	Intermediate Similarity	NPC470167
0.7404	Intermediate Similarity	NPC301787
0.7404	Intermediate Similarity	NPC473701
0.7404	Intermediate Similarity	NPC473526
0.7404	Intermediate Similarity	NPC327093
0.74	Intermediate Similarity	NPC193785
0.74	Intermediate Similarity	NPC476728
0.7396	Intermediate Similarity	NPC473319
0.7396	Intermediate Similarity	NPC131104
0.7396	Intermediate Similarity	NPC3032
0.7391	Intermediate Similarity	NPC71541
0.7391	Intermediate Similarity	NPC211049
0.7391	Intermediate Similarity	NPC116320
0.7391	Intermediate Similarity	NPC119922
0.7387	Intermediate Similarity	NPC240509
0.7387	Intermediate Similarity	NPC204552
0.7387	Intermediate Similarity	NPC297179
0.7387	Intermediate Similarity	NPC470776
0.7387	Intermediate Similarity	NPC188667
0.7383	Intermediate Similarity	NPC470622
0.7379	Intermediate Similarity	NPC275990
0.7374	Intermediate Similarity	NPC217567
0.7374	Intermediate Similarity	NPC76136
0.7374	Intermediate Similarity	NPC329713
0.7368	Intermediate Similarity	NPC91693
0.7368	Intermediate Similarity	NPC120395
0.7368	Intermediate Similarity	NPC18945
0.7368	Intermediate Similarity	NPC105926
0.7368	Intermediate Similarity	NPC265557
0.7368	Intermediate Similarity	NPC248216
0.7364	Intermediate Similarity	NPC207217
0.7364	Intermediate Similarity	NPC474734
0.7363	Intermediate Similarity	NPC275243
0.7363	Intermediate Similarity	NPC474754
0.7358	Intermediate Similarity	NPC231278
0.7358	Intermediate Similarity	NPC316930
0.7358	Intermediate Similarity	NPC153587
0.7358	Intermediate Similarity	NPC218123
0.7358	Intermediate Similarity	NPC112895
0.7353	Intermediate Similarity	NPC477655
0.7347	Intermediate Similarity	NPC165180

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 NPC216137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	492
0.1-0.2	3899
0.2-0.3	3042
0.3-0.4	1014
0.4-0.5	376
0.5-0.6	208
0.6-0.7	116
0.7-0.8	3
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
0.798	Intermediate Similarity	NPD1700	Approved
0.7864	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6921	Approved
0.6944	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6319	Approved
0.6757	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7492	Approved
0.6702	Remote Similarity	NPD6115	Approved
0.6702	Remote Similarity	NPD6118	Approved
0.6702	Remote Similarity	NPD6114	Approved
0.6702	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD1780	Approved
0.6667	Remote Similarity	NPD1779	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6639	Remote Similarity	NPD8328	Phase 3
0.6637	Remote Similarity	NPD8297	Approved
0.6612	Remote Similarity	NPD7078	Approved
0.6612	Remote Similarity	NPD8293	Discontinued
0.6606	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6116	Phase 1
0.6593	Remote Similarity	NPD5777	Approved
0.6559	Remote Similarity	NPD3703	Phase 2
0.6557	Remote Similarity	NPD7736	Approved
0.6555	Remote Similarity	NPD6370	Approved
0.6549	Remote Similarity	NPD6650	Approved
0.6549	Remote Similarity	NPD6649	Approved
0.6545	Remote Similarity	NPD5739	Approved
0.6545	Remote Similarity	NPD6675	Approved
0.6545	Remote Similarity	NPD6008	Approved
0.6545	Remote Similarity	NPD6402	Approved
0.6545	Remote Similarity	NPD7128	Approved
0.6518	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6117	Approved
0.6471	Remote Similarity	NPD6016	Approved
0.6471	Remote Similarity	NPD6015	Approved
0.6444	Remote Similarity	NPD229	Approved
0.6429	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD6881	Approved
0.6417	Remote Similarity	NPD5988	Approved
0.6348	Remote Similarity	NPD6882	Approved
0.6339	Remote Similarity	NPD5701	Approved
0.6339	Remote Similarity	NPD5697	Approved
0.6316	Remote Similarity	NPD7102	Approved
0.6316	Remote Similarity	NPD7290	Approved
0.6316	Remote Similarity	NPD6883	Approved
0.6306	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4632	Approved
0.6277	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6009	Approved
0.6261	Remote Similarity	NPD8130	Phase 1
0.6261	Remote Similarity	NPD6847	Approved
0.6261	Remote Similarity	NPD6869	Approved
0.6261	Remote Similarity	NPD6617	Approved
0.623	Remote Similarity	NPD7604	Phase 2
0.6228	Remote Similarity	NPD6012	Approved
0.6228	Remote Similarity	NPD6013	Approved
0.6228	Remote Similarity	NPD6014	Approved
0.6211	Remote Similarity	NPD3702	Approved
0.62	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3669	Approved
0.6198	Remote Similarity	NPD5983	Phase 2
0.619	Remote Similarity	NPD8034	Phase 2
0.619	Remote Similarity	NPD8035	Phase 2
0.616	Remote Similarity	NPD6033	Approved
0.614	Remote Similarity	NPD6011	Approved
0.6129	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6336	Discontinued
0.6126	Remote Similarity	NPD8301	Approved
0.6126	Remote Similarity	NPD8300	Approved
0.6121	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7319	Approved
0.6111	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7900	Approved
0.6064	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6672	Approved
0.6058	Remote Similarity	NPD5737	Approved
0.6034	Remote Similarity	NPD4634	Approved
0.6022	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD8133	Approved
0.5981	Remote Similarity	NPD6399	Phase 3
0.5957	Remote Similarity	NPD4789	Approved
0.5917	Remote Similarity	NPD6274	Approved
0.5914	Remote Similarity	NPD5360	Phase 3
0.5914	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7902	Approved
0.5909	Remote Similarity	NPD4755	Approved
0.5909	Remote Similarity	NPD6084	Phase 2
0.5909	Remote Similarity	NPD6083	Phase 2
0.5902	Remote Similarity	NPD7100	Approved
0.5902	Remote Similarity	NPD7101	Approved
0.5895	Remote Similarity	NPD6081	Approved
0.5873	Remote Similarity	NPD7507	Approved
0.5872	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4224	Phase 2
0.5868	Remote Similarity	NPD7115	Discovery
0.5865	Remote Similarity	NPD6098	Approved
0.5859	Remote Similarity	NPD4802	Phase 2
0.5859	Remote Similarity	NPD4238	Approved
0.5856	Remote Similarity	NPD5696	Approved
0.5856	Remote Similarity	NPD4225	Approved
0.5849	Remote Similarity	NPD6080	Approved
0.5849	Remote Similarity	NPD6673	Approved
0.5849	Remote Similarity	NPD6904	Approved
0.5841	Remote Similarity	NPD8082	Approved
0.5841	Remote Similarity	NPD8084	Approved
0.5841	Remote Similarity	NPD8139	Approved
0.5841	Remote Similarity	NPD8085	Approved
0.5841	Remote Similarity	NPD8138	Approved
0.5841	Remote Similarity	NPD8083	Approved
0.5841	Remote Similarity	NPD8086	Approved
0.5824	Remote Similarity	NPD371	Approved
0.582	Remote Similarity	NPD6335	Approved
0.581	Remote Similarity	NPD3573	Approved
0.5806	Remote Similarity	NPD6908	Approved
0.5806	Remote Similarity	NPD6909	Approved
0.5804	Remote Similarity	NPD5285	Approved
0.5804	Remote Similarity	NPD4700	Approved
0.5804	Remote Similarity	NPD5286	Approved
0.5804	Remote Similarity	NPD4696	Approved
0.5789	Remote Similarity	NPD8276	Approved
0.5789	Remote Similarity	NPD4245	Approved
0.5789	Remote Similarity	NPD4244	Approved
0.5789	Remote Similarity	NPD8275	Approved
0.578	Remote Similarity	NPD7748	Approved
0.578	Remote Similarity	NPD5282	Discontinued
0.5769	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD8081	Approved
0.5738	Remote Similarity	NPD6317	Approved
0.5727	Remote Similarity	NPD5695	Phase 3
0.5726	Remote Similarity	NPD6686	Approved
0.5714	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD6684	Approved
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD7334	Approved
0.5702	Remote Similarity	NPD5224	Approved
0.5702	Remote Similarity	NPD5225	Approved
0.5702	Remote Similarity	NPD5211	Phase 2
0.5702	Remote Similarity	NPD5226	Approved
0.5702	Remote Similarity	NPD4633	Approved
0.5691	Remote Similarity	NPD6313	Approved
0.5691	Remote Similarity	NPD6314	Approved
0.569	Remote Similarity	NPD4768	Approved
0.569	Remote Similarity	NPD4767	Approved
0.569	Remote Similarity	NPD8393	Approved
0.5688	Remote Similarity	NPD8171	Discontinued
0.5684	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD3698	Phase 2
0.568	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.568	Remote Similarity	NPD8515	Approved
0.568	Remote Similarity	NPD8517	Approved
0.568	Remote Similarity	NPD8516	Approved
0.568	Remote Similarity	NPD8513	Phase 3
0.5676	Remote Similarity	NPD4697	Phase 3
0.5664	Remote Similarity	NPD7639	Approved
0.5664	Remote Similarity	NPD7640	Approved
0.5656	Remote Similarity	NPD6868	Approved
0.5656	Remote Similarity	NPD6940	Discontinued
0.5652	Remote Similarity	NPD5175	Approved
0.5652	Remote Similarity	NPD5174	Approved
0.5645	Remote Similarity	NPD7516	Approved
0.5641	Remote Similarity	NPD6412	Phase 2
0.5641	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD2687	Approved
0.5625	Remote Similarity	NPD2254	Approved
0.5625	Remote Similarity	NPD2686	Approved
0.5619	Remote Similarity	NPD1694	Approved
0.5614	Remote Similarity	NPD5223	Approved
0.5607	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6903	Approved
0.5603	Remote Similarity	NPD5141	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