NPASS Compound

Structure

CID112780 OpenBabel06191715462D 36 38 0 0 1 0 0 0 0 0999 V2000 1.1133 1.3268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2660 -3.2409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2660 0.2232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1245 1.6276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1585 -0.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8164 -1.7509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0629 -1.0668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8905 -0.3008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2981 0.0413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5321 -1.2856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2981 -2.3268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9397 0.3420 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2660 -3.2409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7660 1.0893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1848 1.9696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2981 -1.3268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 -1.6276 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8905 -0.9848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7057 -0.3008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7057 -0.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2660 -1.5088 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2660 0.2232 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5924 0.3420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1736 -0.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7057 -0.3008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1642 -2.8268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7660 -4.1069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2660 1.9553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0111 2.9544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7566 -1.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6454 0.0413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9764 0.2162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7660 -2.3748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7660 1.0893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4187 1.3268 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 19 1 0 0 0 0 11 16 1 0 0 0 0 11 27 1 0 0 0 0 12 19 1 0 0 0 0 12 26 1 6 0 0 0 13 28 2 0 0 0 0 13 34 1 0 0 0 0 14 29 2 0 0 0 0 14 35 1 0 0 0 0 15 30 2 0 0 0 0 15 36 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 10 1 6 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 18 31 1 6 0 0 0 19 32 2 0 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 34 1 6 0 0 0 22 23 1 0 0 0 0 22 25 1 6 0 0 0 22 35 1 0 0 0 0 23 26 1 1 0 0 0 23 36 1 0 0 0 0 24 26 1 0 0 0 0 25 7 1 1 0 0 0 26 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.25
Volume:	507.303
LogP:	0.88
LogD:	0.547
LogS:	-3.038
# Rotatable Bonds:	7
TPSA:	156.66
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.285
Synthetic Accessibility Score:	5.883
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
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:	-5.277
MDCK Permeability:	7.872012065490708e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.729
20% Bioavailability (F20%):	0.404
30% Bioavailability (F30%):	0.694

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	43.867828369140625%
Volume Distribution (VD):	0.897
Pgp-substrate:	40.17976760864258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.243
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	2.069
Half-life (T1/2):	0.812

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.838
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.665
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.115
Carcinogencity:	0.323
Eye Corrosion:	0.004
Eye Irritation:	0.043
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC112780

Natural Product ID:	NPC112780
*Common Name:**	ZMMCRUZQJGEEQT-VBWYYGPTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZMMCRUZQJGEEQT-VBWYYGPTSA-N
Standard InCHI:	InChI=1S/C26H38O10/c1-12-19(32)10-17-21(34-13(2)28)20-16(11-27)18(31)8-9-25(20,7)22(35-14(3)29)23(36-15(4)30)26(12,33)24(17,5)6/h12,17-18,21-23,27,31,33H,8-11H2,1-7H3/t12-,17+,18+,21-,22+,23+,25-,26+/m1/s1
SMILES:	OCC1=C2[C@H](OC(=O)C)[C@@H]3CC(=O)[C@H]([C@@](C3(C)C)([C@H]([C@@H]([C@@]2(CC[C@@H]1O)C)OC(=O)C)OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL43192
PubChem CID:	10577632
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]
NPO33211	japanese yew	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9873389]
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
IC50	2
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[556225]
NPT2	Others	Unspecified		VCR accumulation	=	219.0	n.a.	PMID[556225]
NPT2	Others	Unspecified		VCR accumulation	=	203.0	n.a.	PMID[556225]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.6	ug.mL-1	PMID[556225]

☑ 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 NPC112780 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	265
0.1-0.2	1650
0.2-0.3	4593
0.3-0.4	7393
0.4-0.5	13458
0.5-0.6	8160
0.6-0.7	5830
0.7-0.8	1305
0.8-0.85	31
0.85-0.9	11
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9126	High Similarity	NPC151393
0.8942	High Similarity	NPC472439
0.8942	High Similarity	NPC469916
0.8846	High Similarity	NPC143609
0.875	High Similarity	NPC111952
0.8738	High Similarity	NPC99266
0.8738	High Similarity	NPC159533
0.8738	High Similarity	NPC8196
0.8641	High Similarity	NPC137430
0.8641	High Similarity	NPC295791
0.8611	High Similarity	NPC269530
0.8544	High Similarity	NPC97435
0.8515	High Similarity	NPC129569
0.8476	Intermediate Similarity	NPC258532
0.8476	Intermediate Similarity	NPC146731
0.8476	Intermediate Similarity	NPC296950
0.844	Intermediate Similarity	NPC317687
0.8416	Intermediate Similarity	NPC471786
0.8416	Intermediate Similarity	NPC37603
0.8364	Intermediate Similarity	NPC471204
0.8349	Intermediate Similarity	NPC317107
0.8349	Intermediate Similarity	NPC157476
0.8333	Intermediate Similarity	NPC284194
0.8333	Intermediate Similarity	NPC471765
0.8333	Intermediate Similarity	NPC4021
0.8333	Intermediate Similarity	NPC159456
0.8333	Intermediate Similarity	NPC221801
0.8333	Intermediate Similarity	NPC211810
0.8317	Intermediate Similarity	NPC472416
0.8317	Intermediate Similarity	NPC182826
0.8317	Intermediate Similarity	NPC472360
0.8317	Intermediate Similarity	NPC105375
0.8304	Intermediate Similarity	NPC55296
0.8302	Intermediate Similarity	NPC470104
0.8302	Intermediate Similarity	NPC65523
0.8288	Intermediate Similarity	NPC181145
0.8288	Intermediate Similarity	NPC117712
0.8286	Intermediate Similarity	NPC474709
0.8269	Intermediate Similarity	NPC79303
0.8269	Intermediate Similarity	NPC188968
0.8261	Intermediate Similarity	NPC269642
0.8257	Intermediate Similarity	NPC5103
0.8257	Intermediate Similarity	NPC235014
0.8257	Intermediate Similarity	NPC83005
0.8246	Intermediate Similarity	NPC268530
0.8246	Intermediate Similarity	NPC154491
0.8246	Intermediate Similarity	NPC251226
0.823	Intermediate Similarity	NPC251310
0.8224	Intermediate Similarity	NPC470587
0.8224	Intermediate Similarity	NPC123726
0.8224	Intermediate Similarity	NPC284365
0.8218	Intermediate Similarity	NPC99653
0.8208	Intermediate Similarity	NPC69171
0.8208	Intermediate Similarity	NPC474165
0.8205	Intermediate Similarity	NPC181999
0.8198	Intermediate Similarity	NPC311592
0.8198	Intermediate Similarity	NPC469454
0.8198	Intermediate Similarity	NPC75167
0.8198	Intermediate Similarity	NPC469463
0.8198	Intermediate Similarity	NPC469496
0.8198	Intermediate Similarity	NPC25909
0.819	Intermediate Similarity	NPC469789
0.819	Intermediate Similarity	NPC67251
0.8174	Intermediate Similarity	NPC46570
0.8165	Intermediate Similarity	NPC42662
0.8165	Intermediate Similarity	NPC273433
0.8158	Intermediate Similarity	NPC77689
0.8158	Intermediate Similarity	NPC473636
0.8158	Intermediate Similarity	NPC230513
0.8148	Intermediate Similarity	NPC230541
0.8148	Intermediate Similarity	NPC187435
0.8148	Intermediate Similarity	NPC67321
0.8142	Intermediate Similarity	NPC134430
0.8142	Intermediate Similarity	NPC476712
0.8142	Intermediate Similarity	NPC476713
0.8142	Intermediate Similarity	NPC469684
0.8142	Intermediate Similarity	NPC470775
0.8142	Intermediate Similarity	NPC176513
0.8142	Intermediate Similarity	NPC473590
0.8131	Intermediate Similarity	NPC475036
0.812	Intermediate Similarity	NPC470922
0.812	Intermediate Similarity	NPC476729
0.8119	Intermediate Similarity	NPC124374
0.8113	Intermediate Similarity	NPC80781
0.8113	Intermediate Similarity	NPC183571
0.8108	Intermediate Similarity	NPC476801
0.8108	Intermediate Similarity	NPC174836
0.8108	Intermediate Similarity	NPC472002
0.8103	Intermediate Similarity	NPC23786
0.8103	Intermediate Similarity	NPC107493
0.8103	Intermediate Similarity	NPC470265
0.8095	Intermediate Similarity	NPC474718
0.8095	Intermediate Similarity	NPC476933
0.8095	Intermediate Similarity	NPC271295
0.8095	Intermediate Similarity	NPC198880
0.8087	Intermediate Similarity	NPC48692
0.8087	Intermediate Similarity	NPC475003
0.8081	Intermediate Similarity	NPC471779
0.8077	Intermediate Similarity	NPC473244
0.8077	Intermediate Similarity	NPC474395
0.8077	Intermediate Similarity	NPC254496
0.8077	Intermediate Similarity	NPC285513
0.8073	Intermediate Similarity	NPC322903
0.8073	Intermediate Similarity	NPC476479
0.8073	Intermediate Similarity	NPC94942
0.8073	Intermediate Similarity	NPC37628
0.8073	Intermediate Similarity	NPC94377
0.807	Intermediate Similarity	NPC470776
0.8053	Intermediate Similarity	NPC474734
0.8053	Intermediate Similarity	NPC476710
0.8053	Intermediate Similarity	NPC476711
0.8051	Intermediate Similarity	NPC203702
0.8051	Intermediate Similarity	NPC120994
0.8051	Intermediate Similarity	NPC293112
0.8037	Intermediate Similarity	NPC475321
0.8034	Intermediate Similarity	NPC91693
0.8034	Intermediate Similarity	NPC105926
0.8034	Intermediate Similarity	NPC265557
0.8034	Intermediate Similarity	NPC18945
0.802	Intermediate Similarity	NPC48732
0.802	Intermediate Similarity	NPC220216
0.8018	Intermediate Similarity	NPC304180
0.8018	Intermediate Similarity	NPC179798
0.8017	Intermediate Similarity	NPC67569
0.8	Intermediate Similarity	NPC141350
0.8	Intermediate Similarity	NPC42673
0.8	Intermediate Similarity	NPC470186
0.8	Intermediate Similarity	NPC475041
0.8	Intermediate Similarity	NPC473839
0.8	Intermediate Similarity	NPC211093
0.7982	Intermediate Similarity	NPC473968
0.7982	Intermediate Similarity	NPC98249
0.7982	Intermediate Similarity	NPC475809
0.7982	Intermediate Similarity	NPC469318
0.7982	Intermediate Similarity	NPC284732
0.7982	Intermediate Similarity	NPC473173
0.7982	Intermediate Similarity	NPC78966
0.7982	Intermediate Similarity	NPC58662
0.7982	Intermediate Similarity	NPC473165
0.7982	Intermediate Similarity	NPC53396
0.7966	Intermediate Similarity	NPC81736
0.7966	Intermediate Similarity	NPC8369
0.7966	Intermediate Similarity	NPC172154
0.7966	Intermediate Similarity	NPC469790
0.7966	Intermediate Similarity	NPC24651
0.7965	Intermediate Similarity	NPC284915
0.7963	Intermediate Similarity	NPC118911
0.7963	Intermediate Similarity	NPC220964
0.7963	Intermediate Similarity	NPC475676
0.7949	Intermediate Similarity	NPC312833
0.7946	Intermediate Similarity	NPC473877
0.7946	Intermediate Similarity	NPC277769
0.7946	Intermediate Similarity	NPC42658
0.7946	Intermediate Similarity	NPC90952
0.7946	Intermediate Similarity	NPC126691
0.7944	Intermediate Similarity	NPC165250
0.7928	Intermediate Similarity	NPC161816
0.7928	Intermediate Similarity	NPC472417
0.7928	Intermediate Similarity	NPC115257
0.7928	Intermediate Similarity	NPC469917
0.7928	Intermediate Similarity	NPC46407
0.7921	Intermediate Similarity	NPC261320
0.7913	Intermediate Similarity	NPC240509
0.7913	Intermediate Similarity	NPC276758
0.7913	Intermediate Similarity	NPC284707
0.7913	Intermediate Similarity	NPC18233
0.7909	Intermediate Similarity	NPC476802
0.7909	Intermediate Similarity	NPC289702
0.7909	Intermediate Similarity	NPC306265
0.7909	Intermediate Similarity	NPC208461
0.7909	Intermediate Similarity	NPC89171
0.7899	Intermediate Similarity	NPC473635
0.7895	Intermediate Similarity	NPC470628
0.7895	Intermediate Similarity	NPC16081
0.7895	Intermediate Similarity	NPC474046
0.7895	Intermediate Similarity	NPC173686
0.7895	Intermediate Similarity	NPC259306
0.7895	Intermediate Similarity	NPC176840
0.7895	Intermediate Similarity	NPC179626
0.789	Intermediate Similarity	NPC127609
0.7885	Intermediate Similarity	NPC134067
0.7885	Intermediate Similarity	NPC477438
0.7885	Intermediate Similarity	NPC477437
0.7881	Intermediate Similarity	NPC472399
0.7881	Intermediate Similarity	NPC11895
0.7876	Intermediate Similarity	NPC208998
0.7876	Intermediate Similarity	NPC250109
0.7876	Intermediate Similarity	NPC7921
0.7876	Intermediate Similarity	NPC56448
0.7876	Intermediate Similarity	NPC962
0.787	Intermediate Similarity	NPC4620
0.787	Intermediate Similarity	NPC72842
0.787	Intermediate Similarity	NPC218513
0.787	Intermediate Similarity	NPC90177
0.787	Intermediate Similarity	NPC55954
0.787	Intermediate Similarity	NPC474775
0.787	Intermediate Similarity	NPC99510
0.7869	Intermediate Similarity	NPC476193
0.7864	Intermediate Similarity	NPC477435
0.7864	Intermediate Similarity	NPC477436

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 NPC112780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	2200
0.2-0.3	3495
0.3-0.4	2013
0.4-0.5	748
0.5-0.6	318
0.6-0.7	119
0.7-0.8	10
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
0.7909	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD7115	Discovery
0.7611	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5778	Approved
0.7524	Intermediate Similarity	NPD5779	Approved
0.7522	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4225	Approved
0.7429	Intermediate Similarity	NPD7983	Approved
0.7417	Intermediate Similarity	NPD8515	Approved
0.7417	Intermediate Similarity	NPD8513	Phase 3
0.7417	Intermediate Similarity	NPD8516	Approved
0.7417	Intermediate Similarity	NPD8517	Approved
0.7345	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6319	Approved
0.7304	Intermediate Similarity	NPD6371	Approved
0.7295	Intermediate Similarity	NPD8328	Phase 3
0.7281	Intermediate Similarity	NPD6686	Approved
0.728	Intermediate Similarity	NPD7319	Approved
0.7273	Intermediate Similarity	NPD6921	Approved
0.7177	Intermediate Similarity	NPD7507	Approved
0.717	Intermediate Similarity	NPD46	Approved
0.717	Intermediate Similarity	NPD6698	Approved
0.712	Intermediate Similarity	NPD8074	Phase 3
0.7117	Intermediate Similarity	NPD7640	Approved
0.7117	Intermediate Similarity	NPD7639	Approved
0.7103	Intermediate Similarity	NPD6411	Approved
0.7069	Intermediate Similarity	NPD6373	Approved
0.7069	Intermediate Similarity	NPD6372	Approved
0.7034	Intermediate Similarity	NPD8297	Approved
0.7027	Intermediate Similarity	NPD7638	Approved
0.6991	Remote Similarity	NPD7632	Discontinued
0.6975	Remote Similarity	NPD4632	Approved
0.696	Remote Similarity	NPD7492	Approved
0.6957	Remote Similarity	NPD6675	Approved
0.6957	Remote Similarity	NPD7128	Approved
0.6957	Remote Similarity	NPD6402	Approved
0.6957	Remote Similarity	NPD5739	Approved
0.6949	Remote Similarity	NPD6649	Approved
0.6949	Remote Similarity	NPD6650	Approved
0.6916	Remote Similarity	NPD6101	Approved
0.6916	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6054	Approved
0.6911	Remote Similarity	NPD6059	Approved
0.6905	Remote Similarity	NPD6616	Approved
0.6903	Remote Similarity	NPD5344	Discontinued
0.6897	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6053	Discontinued
0.6881	Remote Similarity	NPD6399	Phase 3
0.685	Remote Similarity	NPD7078	Approved
0.685	Remote Similarity	NPD8293	Discontinued
0.6838	Remote Similarity	NPD6881	Approved
0.6838	Remote Similarity	NPD6899	Approved
0.6838	Remote Similarity	NPD7320	Approved
0.6833	Remote Similarity	NPD8133	Approved
0.681	Remote Similarity	NPD6008	Approved
0.6807	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6370	Approved
0.6797	Remote Similarity	NPD7736	Approved
0.6786	Remote Similarity	NPD7902	Approved
0.6757	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6412	Phase 2
0.6752	Remote Similarity	NPD5701	Approved
0.6752	Remote Similarity	NPD5697	Approved
0.675	Remote Similarity	NPD6882	Approved
0.6723	Remote Similarity	NPD7102	Approved
0.6723	Remote Similarity	NPD7290	Approved
0.6723	Remote Similarity	NPD4634	Approved
0.6723	Remote Similarity	NPD6883	Approved
0.672	Remote Similarity	NPD6015	Approved
0.672	Remote Similarity	NPD6016	Approved
0.6698	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6641	Remote Similarity	NPD7260	Phase 2
0.6639	Remote Similarity	NPD6013	Approved
0.6639	Remote Similarity	NPD6014	Approved
0.6639	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD7515	Phase 2
0.6636	Remote Similarity	NPD7637	Suspended
0.6614	Remote Similarity	NPD7604	Phase 2
0.6613	Remote Similarity	NPD7328	Approved
0.6613	Remote Similarity	NPD7327	Approved
0.6591	Remote Similarity	NPD6845	Suspended
0.6587	Remote Similarity	NPD8033	Approved
0.6587	Remote Similarity	NPD5983	Phase 2
0.6587	Remote Similarity	NPD7503	Approved
0.6579	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7516	Approved
0.6555	Remote Similarity	NPD6011	Approved
0.6552	Remote Similarity	NPD5211	Phase 2
0.6549	Remote Similarity	NPD7839	Suspended
0.6545	Remote Similarity	NPD7838	Discovery
0.6545	Remote Similarity	NPD5785	Approved
0.6529	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6648	Approved
0.6518	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7900	Approved
0.6512	Remote Similarity	NPD6336	Discontinued
0.6508	Remote Similarity	NPD8294	Approved
0.6508	Remote Similarity	NPD8377	Approved
0.6491	Remote Similarity	NPD6083	Phase 2
0.6491	Remote Similarity	NPD6084	Phase 2
0.6491	Remote Similarity	NPD4755	Approved
0.6481	Remote Similarity	NPD5786	Approved
0.6457	Remote Similarity	NPD8380	Approved
0.6457	Remote Similarity	NPD8296	Approved
0.6457	Remote Similarity	NPD8335	Approved
0.6457	Remote Similarity	NPD8379	Approved
0.6457	Remote Similarity	NPD8378	Approved
0.6455	Remote Similarity	NPD5328	Approved
0.6441	Remote Similarity	NPD5141	Approved
0.6412	Remote Similarity	NPD6033	Approved
0.6385	Remote Similarity	NPD8451	Approved
0.6379	Remote Similarity	NPD5285	Approved
0.6379	Remote Similarity	NPD5286	Approved
0.6379	Remote Similarity	NPD4700	Approved
0.6379	Remote Similarity	NPD4696	Approved
0.6372	Remote Similarity	NPD5282	Discontinued
0.6357	Remote Similarity	NPD7642	Approved
0.6339	Remote Similarity	NPD8035	Phase 2
0.6339	Remote Similarity	NPD8034	Phase 2
0.6339	Remote Similarity	NPD6079	Approved
0.6336	Remote Similarity	NPD8448	Approved
0.633	Remote Similarity	NPD3618	Phase 1
0.633	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6274	Approved
0.6316	Remote Similarity	NPD5695	Phase 3
0.6308	Remote Similarity	NPD8299	Approved
0.6308	Remote Similarity	NPD8342	Approved
0.6308	Remote Similarity	NPD8340	Approved
0.6308	Remote Similarity	NPD8341	Approved
0.6299	Remote Similarity	NPD7100	Approved
0.6299	Remote Similarity	NPD7101	Approved
0.6296	Remote Similarity	NPD4786	Approved
0.6293	Remote Similarity	NPD5696	Approved
0.6273	Remote Similarity	NPD3573	Approved
0.6273	Remote Similarity	NPD7524	Approved
0.6271	Remote Similarity	NPD5225	Approved
0.6271	Remote Similarity	NPD4633	Approved
0.6271	Remote Similarity	NPD5226	Approved
0.6271	Remote Similarity	NPD5224	Approved
0.627	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD3667	Approved
0.6262	Remote Similarity	NPD4270	Approved
0.6262	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4269	Approved
0.6261	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6335	Approved
0.6218	Remote Similarity	NPD5175	Approved
0.6218	Remote Similarity	NPD5174	Approved
0.6204	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD8444	Approved
0.6202	Remote Similarity	NPD6908	Approved
0.6202	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6909	Approved
0.6194	Remote Similarity	NPD8390	Approved
0.6194	Remote Similarity	NPD8392	Approved
0.6194	Remote Similarity	NPD8391	Approved
0.6186	Remote Similarity	NPD5223	Approved
0.6186	Remote Similarity	NPD1700	Approved
0.6182	Remote Similarity	NPD5330	Approved
0.6182	Remote Similarity	NPD6684	Approved
0.6182	Remote Similarity	NPD6409	Approved
0.6182	Remote Similarity	NPD7334	Approved
0.6182	Remote Similarity	NPD7146	Approved
0.6182	Remote Similarity	NPD7521	Approved
0.6174	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5369	Approved
0.6159	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8080	Discontinued
0.6148	Remote Similarity	NPD4730	Approved
0.6148	Remote Similarity	NPD4729	Approved
0.6147	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6317	Approved
0.614	Remote Similarity	NPD4202	Approved
0.6136	Remote Similarity	NPD8273	Phase 1
0.6121	Remote Similarity	NPD5221	Approved
0.6121	Remote Similarity	NPD5222	Approved
0.6121	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6435	Approved
0.6107	Remote Similarity	NPD7830	Approved
0.6107	Remote Similarity	NPD7829	Approved
0.6094	Remote Similarity	NPD6313	Approved
0.6094	Remote Similarity	NPD6314	Approved
0.6091	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5363	Approved
0.6083	Remote Similarity	NPD4754	Approved
0.6077	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4252	Approved
0.6071	Remote Similarity	NPD6672	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