NPASS Compound

Structure

NPC472439 OpenBabel07101719512D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.6927 -3.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9165 1.9822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8299 -5.0514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2907 -4.6598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3890 -0.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7717 -1.4966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9748 -1.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4025 -1.1348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9695 -2.5038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2992 1.0583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4473 -4.1275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2992 -4.7904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0731 -0.6589 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3564 -1.9558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7802 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0731 -0.6589 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0731 -3.0731 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3660 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0731 -3.0731 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7802 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2907 0.9278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0560 -3.3342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9165 -5.7142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4325 -2.3385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 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 -0.6904 0.2650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4558 -3.9970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6904 -3.9970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 25 1 0 0 0 0 10 17 1 0 0 0 0 11 32 1 0 0 0 0 12 17 1 0 0 0 0 12 19 2 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 10 1 1 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 17 30 2 0 0 0 0 18 26 1 1 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 20 22 1 0 0 0 0 20 33 1 1 0 0 0 21 23 1 0 0 0 0 21 34 1 6 0 0 0 22 25 1 6 0 0 0 22 26 1 0 0 0 0 23 25 1 1 0 0 0 23 35 1 0 0 0 0 25 7 1 6 0 0 0 26 11 1 6 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.24
Volume:	489.956
LogP:	2.33
LogD:	1.626
LogS:	-3.901
# Rotatable Bonds:	6
TPSA:	128.73
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	6.177
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.302
MDCK Permeability:	7.685110904276371e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.495
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.446
Plasma Protein Binding (PPB):	72.90457153320312%
Volume Distribution (VD):	1.187
Pgp-substrate:	26.814640045166016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.351
CYP3A4-substrate:	0.37

ADMET: Excretion

Clearance (CL):	2.939
Half-life (T1/2):	0.852

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.872
Drug-inuced Liver Injury (DILI):	0.845
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.648
Skin Sensitization:	0.482
Carcinogencity:	0.045
Eye Corrosion:	0.007
Eye Irritation:	0.018
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC472439

Natural Product ID:	NPC472439
*Common Name:**	WOZSNJQYEVOUIT-ZZNHCZCLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WOZSNJQYEVOUIT-ZZNHCZCLSA-N
Standard InCHI:	InChI=1S/C26H36O9/c1-12-17(30)10-16-20(33-13(2)27)22-25(7,9-8-18(31)26(22)11-32-26)23(35-15(4)29)21(34-14(3)28)19(12)24(16,5)6/h16,18,20-23,31H,8-11H2,1-7H3/t16-,18-,20+,21+,22-,23-,25+,26-/m0/s1
SMILES:	CC(=O)O[C@@H]1C2=C(C)C(=O)C[C@H](C2(C)C)[C@H]([C@H]2[C@@]([C@H]1OC(=O)C)(C)CC[C@@H]([C@@]12OC1)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL340817
PubChem CID:	15378575
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes 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
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	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
Others	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Control	=	180.0	%	PMID[464217]
NPT2	Others	Unspecified	Control	=	364.0	%	PMID[464217]
NPT2	Others	Unspecified	Activity	=	28.0	%	PMID[464218]

☑ 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 NPC472439 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	270
0.1-0.2	1670
0.2-0.3	4724
0.3-0.4	7794
0.4-0.5	13770
0.5-0.6	7786
0.6-0.7	5440
0.7-0.8	1180
0.8-0.85	47
0.85-0.9	14
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469916
0.9126	High Similarity	NPC143609
0.9038	High Similarity	NPC151393
0.9029	High Similarity	NPC111952
0.902	High Similarity	NPC99266
0.902	High Similarity	NPC8196
0.8942	High Similarity	NPC112780
0.8922	High Similarity	NPC137430
0.8911	High Similarity	NPC79303
0.8868	High Similarity	NPC469917
0.8868	High Similarity	NPC472417
0.8824	High Similarity	NPC97435
0.8725	High Similarity	NPC271295
0.8704	High Similarity	NPC317687
0.8654	High Similarity	NPC159533
0.8614	High Similarity	NPC129569
0.8611	High Similarity	NPC317107
0.8598	High Similarity	NPC299590
0.8571	High Similarity	NPC65523
0.8558	High Similarity	NPC295791
0.8544	High Similarity	NPC188968
0.8496	Intermediate Similarity	NPC251226
0.8455	Intermediate Similarity	NPC471204
0.8447	Intermediate Similarity	NPC222303
0.844	Intermediate Similarity	NPC469655
0.844	Intermediate Similarity	NPC469656
0.844	Intermediate Similarity	NPC474846
0.8421	Intermediate Similarity	NPC159456
0.8421	Intermediate Similarity	NPC4021
0.8416	Intermediate Similarity	NPC182826
0.8416	Intermediate Similarity	NPC105375
0.8411	Intermediate Similarity	NPC187435
0.8411	Intermediate Similarity	NPC67321
0.8381	Intermediate Similarity	NPC165250
0.8381	Intermediate Similarity	NPC472552
0.8364	Intermediate Similarity	NPC42658
0.8348	Intermediate Similarity	NPC23786
0.8348	Intermediate Similarity	NPC470265
0.8333	Intermediate Similarity	NPC154491
0.8333	Intermediate Similarity	NPC268530
0.8333	Intermediate Similarity	NPC94942
0.8333	Intermediate Similarity	NPC322903
0.8288	Intermediate Similarity	NPC477126
0.8286	Intermediate Similarity	NPC472554
0.8261	Intermediate Similarity	NPC67569
0.8257	Intermediate Similarity	NPC475586
0.8252	Intermediate Similarity	NPC221801
0.8252	Intermediate Similarity	NPC284194
0.8252	Intermediate Similarity	NPC211810
0.8252	Intermediate Similarity	NPC471765
0.8246	Intermediate Similarity	NPC42673
0.8235	Intermediate Similarity	NPC472360
0.8235	Intermediate Similarity	NPC472416
0.823	Intermediate Similarity	NPC13713
0.823	Intermediate Similarity	NPC98249
0.823	Intermediate Similarity	NPC469684
0.823	Intermediate Similarity	NPC58662
0.823	Intermediate Similarity	NPC53396
0.8224	Intermediate Similarity	NPC146731
0.8224	Intermediate Similarity	NPC296950
0.8208	Intermediate Similarity	NPC476081
0.8205	Intermediate Similarity	NPC469790
0.8198	Intermediate Similarity	NPC269530
0.8198	Intermediate Similarity	NPC472002
0.8182	Intermediate Similarity	NPC472215
0.8182	Intermediate Similarity	NPC253906
0.8182	Intermediate Similarity	NPC472214
0.8182	Intermediate Similarity	NPC471779
0.8165	Intermediate Similarity	NPC306265
0.8165	Intermediate Similarity	NPC94377
0.8165	Intermediate Similarity	NPC476479
0.8158	Intermediate Similarity	NPC124676
0.8158	Intermediate Similarity	NPC284707
0.8158	Intermediate Similarity	NPC146280
0.8155	Intermediate Similarity	NPC37603
0.8155	Intermediate Similarity	NPC471786
0.8148	Intermediate Similarity	NPC472389
0.8142	Intermediate Similarity	NPC471127
0.8142	Intermediate Similarity	NPC234858
0.8142	Intermediate Similarity	NPC154363
0.8137	Intermediate Similarity	NPC99653
0.8136	Intermediate Similarity	NPC203702
0.8136	Intermediate Similarity	NPC120994
0.8136	Intermediate Similarity	NPC293112
0.8136	Intermediate Similarity	NPC473635
0.8131	Intermediate Similarity	NPC61442
0.8125	Intermediate Similarity	NPC25909
0.812	Intermediate Similarity	NPC469789
0.812	Intermediate Similarity	NPC11895
0.8103	Intermediate Similarity	NPC310511
0.8091	Intermediate Similarity	NPC273433
0.8091	Intermediate Similarity	NPC87335
0.8091	Intermediate Similarity	NPC469370
0.8087	Intermediate Similarity	NPC77689
0.8087	Intermediate Similarity	NPC475775
0.8087	Intermediate Similarity	NPC475041
0.8087	Intermediate Similarity	NPC476529
0.8087	Intermediate Similarity	NPC473636
0.8077	Intermediate Similarity	NPC91439
0.8073	Intermediate Similarity	NPC471783
0.8073	Intermediate Similarity	NPC9457
0.8073	Intermediate Similarity	NPC473173
0.8073	Intermediate Similarity	NPC473586
0.8073	Intermediate Similarity	NPC469318
0.8073	Intermediate Similarity	NPC180744
0.807	Intermediate Similarity	NPC134430
0.807	Intermediate Similarity	NPC55296
0.807	Intermediate Similarity	NPC473590
0.807	Intermediate Similarity	NPC473968
0.807	Intermediate Similarity	NPC10721
0.8053	Intermediate Similarity	NPC284915
0.8053	Intermediate Similarity	NPC472400
0.8051	Intermediate Similarity	NPC172154
0.8051	Intermediate Similarity	NPC81736
0.8039	Intermediate Similarity	NPC124374
0.8037	Intermediate Similarity	NPC469316
0.8036	Intermediate Similarity	NPC476801
0.8036	Intermediate Similarity	NPC473877
0.8034	Intermediate Similarity	NPC162009
0.8034	Intermediate Similarity	NPC170538
0.8034	Intermediate Similarity	NPC269642
0.8034	Intermediate Similarity	NPC257017
0.802	Intermediate Similarity	NPC261320
0.8018	Intermediate Similarity	NPC5103
0.8018	Intermediate Similarity	NPC235014
0.8017	Intermediate Similarity	NPC475885
0.8017	Intermediate Similarity	NPC48692
0.8017	Intermediate Similarity	NPC107338
0.8017	Intermediate Similarity	NPC109607
0.8017	Intermediate Similarity	NPC157252
0.8017	Intermediate Similarity	NPC145182
0.8017	Intermediate Similarity	NPC471126
0.8017	Intermediate Similarity	NPC471128
0.8	Intermediate Similarity	NPC186525
0.8	Intermediate Similarity	NPC175351
0.8	Intermediate Similarity	NPC325054
0.8	Intermediate Similarity	NPC50774
0.8	Intermediate Similarity	NPC251310
0.8	Intermediate Similarity	NPC151681
0.8	Intermediate Similarity	NPC291564
0.8	Intermediate Similarity	NPC475263
0.8	Intermediate Similarity	NPC293850
0.8	Intermediate Similarity	NPC709
0.8	Intermediate Similarity	NPC121402
0.8	Intermediate Similarity	NPC473244
0.8	Intermediate Similarity	NPC240509
0.8	Intermediate Similarity	NPC224356
0.8	Intermediate Similarity	NPC132753
0.7982	Intermediate Similarity	NPC470587
0.7982	Intermediate Similarity	NPC40632
0.7982	Intermediate Similarity	NPC102352
0.7982	Intermediate Similarity	NPC251236
0.7982	Intermediate Similarity	NPC470980
0.7982	Intermediate Similarity	NPC181357
0.7982	Intermediate Similarity	NPC96312
0.7982	Intermediate Similarity	NPC328374
0.7981	Intermediate Similarity	NPC477437
0.7981	Intermediate Similarity	NPC477438
0.7966	Intermediate Similarity	NPC105926
0.7966	Intermediate Similarity	NPC91693
0.7966	Intermediate Similarity	NPC67251
0.7966	Intermediate Similarity	NPC18945
0.7966	Intermediate Similarity	NPC265557
0.7965	Intermediate Similarity	NPC75167
0.7965	Intermediate Similarity	NPC49451
0.7965	Intermediate Similarity	NPC472757
0.7965	Intermediate Similarity	NPC475966
0.7965	Intermediate Similarity	NPC962
0.7965	Intermediate Similarity	NPC469463
0.7965	Intermediate Similarity	NPC159333
0.7965	Intermediate Similarity	NPC317210
0.7965	Intermediate Similarity	NPC311592
0.7965	Intermediate Similarity	NPC250109
0.7965	Intermediate Similarity	NPC469454
0.7965	Intermediate Similarity	NPC469496
0.7963	Intermediate Similarity	NPC474165
0.7963	Intermediate Similarity	NPC471208
0.7963	Intermediate Similarity	NPC69171
0.7963	Intermediate Similarity	NPC478057
0.7963	Intermediate Similarity	NPC23584
0.7963	Intermediate Similarity	NPC474822
0.7963	Intermediate Similarity	NPC120321
0.7961	Intermediate Similarity	NPC110022
0.7961	Intermediate Similarity	NPC477436
0.7961	Intermediate Similarity	NPC477435
0.7949	Intermediate Similarity	NPC52839
0.7946	Intermediate Similarity	NPC188738
0.7941	Intermediate Similarity	NPC48732
0.7941	Intermediate Similarity	NPC220216
0.7931	Intermediate Similarity	NPC472667
0.7931	Intermediate Similarity	NPC473839
0.7931	Intermediate Similarity	NPC470186
0.7931	Intermediate Similarity	NPC156745
0.7931	Intermediate Similarity	NPC236918
0.7931	Intermediate Similarity	NPC211093
0.7931	Intermediate Similarity	NPC230513
0.7928	Intermediate Similarity	NPC42662
0.7928	Intermediate Similarity	NPC472216
0.7928	Intermediate Similarity	NPC5475
0.7928	Intermediate Similarity	NPC284828

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 NPC472439 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	2189
0.2-0.3	3545
0.3-0.4	2046
0.4-0.5	724
0.5-0.6	269
0.6-0.7	103
0.7-0.8	10
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8598	High Similarity	NPD4061	Clinical (unspecified phase)
0.8519	High Similarity	NPD5955	Clinical (unspecified phase)
0.8241	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD7115	Discovery
0.7768	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD46	Approved
0.7767	Intermediate Similarity	NPD6698	Approved
0.7615	Intermediate Similarity	NPD5344	Discontinued
0.7522	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6686	Approved
0.7431	Intermediate Similarity	NPD7638	Approved
0.7431	Intermediate Similarity	NPD4225	Approved
0.7364	Intermediate Similarity	NPD7640	Approved
0.7364	Intermediate Similarity	NPD7639	Approved
0.7258	Intermediate Similarity	NPD7507	Approved
0.7241	Intermediate Similarity	NPD6371	Approved
0.7232	Intermediate Similarity	NPD7632	Discontinued
0.7207	Intermediate Similarity	NPD6648	Approved
0.7193	Intermediate Similarity	NPD6008	Approved
0.7182	Intermediate Similarity	NPD7902	Approved
0.7167	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6373	Approved
0.7155	Intermediate Similarity	NPD6372	Approved
0.7131	Intermediate Similarity	NPD6319	Approved
0.7119	Intermediate Similarity	NPD8297	Approved
0.7103	Intermediate Similarity	NPD7838	Discovery
0.7097	Intermediate Similarity	NPD8328	Phase 3
0.7087	Intermediate Similarity	NPD7319	Approved
0.7064	Intermediate Similarity	NPD7748	Approved
0.7059	Intermediate Similarity	NPD4632	Approved
0.7049	Intermediate Similarity	NPD7516	Approved
0.7043	Intermediate Similarity	NPD6675	Approved
0.7043	Intermediate Similarity	NPD7128	Approved
0.7043	Intermediate Similarity	NPD5739	Approved
0.7043	Intermediate Similarity	NPD6402	Approved
0.7037	Intermediate Similarity	NPD7515	Phase 2
0.7034	Intermediate Similarity	NPD6649	Approved
0.7034	Intermediate Similarity	NPD6650	Approved
0.6983	Remote Similarity	NPD6412	Phase 2
0.6972	Remote Similarity	NPD6399	Phase 3
0.6967	Remote Similarity	NPD7328	Approved
0.6967	Remote Similarity	NPD7327	Approved
0.6952	Remote Similarity	NPD1694	Approved
0.6935	Remote Similarity	NPD6921	Approved
0.6935	Remote Similarity	NPD8033	Approved
0.6923	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6917	Remote Similarity	NPD8133	Approved
0.6909	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7900	Approved
0.6855	Remote Similarity	NPD8377	Approved
0.6855	Remote Similarity	NPD8294	Approved
0.6838	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5701	Approved
0.6838	Remote Similarity	NPD5697	Approved
0.6833	Remote Similarity	NPD6882	Approved
0.6833	Remote Similarity	NPD6053	Discontinued
0.6825	Remote Similarity	NPD7604	Phase 2
0.6807	Remote Similarity	NPD7290	Approved
0.6807	Remote Similarity	NPD6883	Approved
0.6807	Remote Similarity	NPD7102	Approved
0.68	Remote Similarity	NPD7503	Approved
0.68	Remote Similarity	NPD8380	Approved
0.68	Remote Similarity	NPD8515	Approved
0.68	Remote Similarity	NPD8379	Approved
0.68	Remote Similarity	NPD8517	Approved
0.68	Remote Similarity	NPD8513	Phase 3
0.68	Remote Similarity	NPD8378	Approved
0.68	Remote Similarity	NPD8296	Approved
0.68	Remote Similarity	NPD8516	Approved
0.68	Remote Similarity	NPD8335	Approved
0.6772	Remote Similarity	NPD7492	Approved
0.675	Remote Similarity	NPD6847	Approved
0.675	Remote Similarity	NPD6869	Approved
0.675	Remote Similarity	NPD8130	Phase 1
0.675	Remote Similarity	NPD6617	Approved
0.6748	Remote Similarity	NPD6009	Approved
0.6729	Remote Similarity	NPD3618	Phase 1
0.6726	Remote Similarity	NPD6084	Phase 2
0.6726	Remote Similarity	NPD6083	Phase 2
0.6723	Remote Similarity	NPD6014	Approved
0.6723	Remote Similarity	NPD6012	Approved
0.6723	Remote Similarity	NPD6013	Approved
0.672	Remote Similarity	NPD6059	Approved
0.672	Remote Similarity	NPD6054	Approved
0.6719	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6011	Approved
0.6615	Remote Similarity	NPD7736	Approved
0.6614	Remote Similarity	NPD6370	Approved
0.6612	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7260	Phase 2
0.6589	Remote Similarity	NPD6336	Discontinued
0.6579	Remote Similarity	NPD4755	Approved
0.6577	Remote Similarity	NPD7983	Approved
0.6552	Remote Similarity	NPD4159	Approved
0.6549	Remote Similarity	NPD5695	Phase 3
0.6549	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5328	Approved
0.6541	Remote Similarity	NPD6845	Suspended
0.6538	Remote Similarity	NPD8074	Phase 3
0.6535	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD6016	Approved
0.6529	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD5696	Approved
0.6518	Remote Similarity	NPD4202	Approved
0.6509	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5211	Phase 2
0.6484	Remote Similarity	NPD5988	Approved
0.6466	Remote Similarity	NPD5285	Approved
0.6466	Remote Similarity	NPD4700	Approved
0.6466	Remote Similarity	NPD5286	Approved
0.6466	Remote Similarity	NPD4696	Approved
0.6429	Remote Similarity	NPD8035	Phase 2
0.6429	Remote Similarity	NPD6079	Approved
0.6429	Remote Similarity	NPD8034	Phase 2
0.6429	Remote Similarity	NPD6411	Approved
0.6422	Remote Similarity	NPD6684	Approved
0.6422	Remote Similarity	NPD7521	Approved
0.6422	Remote Similarity	NPD7334	Approved
0.6422	Remote Similarity	NPD6409	Approved
0.6422	Remote Similarity	NPD7146	Approved
0.6422	Remote Similarity	NPD5330	Approved
0.6404	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6274	Approved
0.6389	Remote Similarity	NPD4786	Approved
0.6387	Remote Similarity	NPD5141	Approved
0.6378	Remote Similarity	NPD7100	Approved
0.6378	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD3573	Approved
0.6356	Remote Similarity	NPD4633	Approved
0.6356	Remote Similarity	NPD5224	Approved
0.6356	Remote Similarity	NPD5226	Approved
0.6356	Remote Similarity	NPD5225	Approved
0.6355	Remote Similarity	NPD3667	Approved
0.6348	Remote Similarity	NPD4697	Phase 3
0.6339	Remote Similarity	NPD5785	Approved
0.6333	Remote Similarity	NPD4768	Approved
0.6333	Remote Similarity	NPD4767	Approved
0.633	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5282	Discontinued
0.6308	Remote Similarity	NPD7642	Approved
0.6308	Remote Similarity	NPD6067	Discontinued
0.6306	Remote Similarity	NPD6903	Approved
0.6306	Remote Similarity	NPD6672	Approved
0.6306	Remote Similarity	NPD5737	Approved
0.6306	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5174	Approved
0.6303	Remote Similarity	NPD5175	Approved
0.6299	Remote Similarity	NPD6335	Approved
0.6283	Remote Similarity	NPD5693	Phase 1
0.6283	Remote Similarity	NPD5281	Approved
0.6283	Remote Similarity	NPD5284	Approved
0.6279	Remote Similarity	NPD6908	Approved
0.6279	Remote Similarity	NPD6909	Approved
0.6273	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD1695	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.6241	Remote Similarity	NPD6033	Approved
0.6239	Remote Similarity	NPD3665	Phase 1
0.6239	Remote Similarity	NPD3666	Approved
0.6239	Remote Similarity	NPD3133	Approved
0.623	Remote Similarity	NPD4729	Approved
0.623	Remote Similarity	NPD4730	Approved
0.622	Remote Similarity	NPD6317	Approved
0.6216	Remote Similarity	NPD7524	Approved
0.6207	Remote Similarity	NPD5221	Approved
0.6207	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5222	Approved
0.6182	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6001	Approved
0.6172	Remote Similarity	NPD6313	Approved
0.6172	Remote Similarity	NPD6314	Approved
0.6167	Remote Similarity	NPD4754	Approved
0.6154	Remote Similarity	NPD5173	Approved
0.6154	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6110	Phase 1
0.6142	Remote Similarity	NPD6868	Approved
0.614	Remote Similarity	NPD7637	Suspended
0.6134	Remote Similarity	NPD1700	Approved
0.6132	Remote Similarity	NPD6697	Approved
0.6132	Remote Similarity	NPD6118	Approved
0.6132	Remote Similarity	NPD6115	Approved
0.6132	Remote Similarity	NPD6114	Approved
0.6129	Remote Similarity	NPD5247	Approved
0.6129	Remote Similarity	NPD5251	Approved
0.6129	Remote Similarity	NPD5249	Phase 3
0.6129	Remote Similarity	NPD5250	Approved
0.6129	Remote Similarity	NPD5248	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