NPASS Compound

Structure

CID111952 OpenBabel06191715462D 34 36 0 0 1 0 0 0 0 0999 V2000 0.5924 -2.0261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4115 0.6015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4584 2.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9927 1.3268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0603 3.1221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2969 0.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0451 -0.5157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4397 -1.2080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0530 -1.6688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1848 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 -1.0261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6454 -0.0413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4584 1.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2267 1.9696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4397 2.2561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1133 -1.3268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.6840 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8191 -1.0261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1848 -0.6840 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 -1.7057 0.3008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1133 0.6428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4397 0.5240 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9397 -0.3420 0.0000 C 0 0 0 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 2.3244 1.3420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4003 2.9544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4397 2.2561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7588 -1.3681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0508 -1.1840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5924 1.3420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2870 1.6276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0603 1.3900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 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 16 1 0 0 0 0 6 25 1 0 0 0 0 7 25 1 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 22 2 0 0 0 0 14 27 2 0 0 0 0 14 32 1 0 0 0 0 15 28 2 0 0 0 0 15 33 1 0 0 0 0 16 29 2 0 0 0 0 16 34 1 0 0 0 0 17 9 1 6 0 0 0 17 25 1 0 0 0 0 18 26 1 1 0 0 0 19 30 2 0 0 0 0 20 31 1 6 0 0 0 21 26 1 1 0 0 0 21 32 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 24 1 0 0 0 0 23 33 1 1 0 0 0 24 26 1 6 0 0 0 24 34 1 0 0 0 0 26 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.24
Volume:	487.086
LogP:	2.667
LogD:	2.74
LogS:	-4.362
# Rotatable Bonds:	6
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	5.486
Fsp3:	0.692
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.086
MDCK Permeability:	7.896310853539035e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.947
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.643

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.571
Plasma Protein Binding (PPB):	64.5924301147461%
Volume Distribution (VD):	1.25
Pgp-substrate:	36.22597122192383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.453
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.35
CYP3A4-substrate:	0.379

ADMET: Excretion

Clearance (CL):	3.298
Half-life (T1/2):	0.277

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.726
Drug-inuced Liver Injury (DILI):	0.775
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.919
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.156
Carcinogencity:	0.136
Eye Corrosion:	0.02
Eye Irritation:	0.029
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC111952

Natural Product ID:	NPC111952
*Common Name:**	NRJCBPQELYLDFN-VCTMJJASSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NRJCBPQELYLDFN-VCTMJJASSA-N
Standard InCHI:	InChI=1S/C26H36O8/c1-12-18-9-17-10-19(30)13(2)22(25(17,6)7)23(33-15(4)28)24(34-16(5)29)26(18,8)21(11-20(12)31)32-14(3)27/h17-18,20-21,23-24,31H,1,9-11H2,2-8H3/t17-,18-,20+,21+,23-,24+,26+/m1/s1
SMILES:	C=C1[C@H]2C[C@@H]3CC(=O)C(=C([C@H]([C@@H]([C@]2(C)[C@H](C[C@@H]1O)OC(=O)C)OC(=O)C)OC(=O)C)C3(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL430628
PubChem CID:	10814443
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]
NPO23840	Taxus x media	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]
NPO23840	Taxus x media	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]
NPO23840	Taxus x media	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]
NPO23840	Taxus x media	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	12302687.71	nM	PMID[488970]

☑ 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 NPC111952 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	228
0.1-0.2	1356
0.2-0.3	3973
0.3-0.4	6443
0.4-0.5	14325
0.5-0.6	8150
0.6-0.7	6576
0.7-0.8	1577
0.8-0.85	37
0.85-0.9	20
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9898	High Similarity	NPC143609
0.9592	High Similarity	NPC8196
0.949	High Similarity	NPC137430
0.9394	High Similarity	NPC99266
0.9216	High Similarity	NPC151393
0.9192	High Similarity	NPC97435
0.9175	High Similarity	NPC211810
0.9175	High Similarity	NPC284194
0.9175	High Similarity	NPC221801
0.9175	High Similarity	NPC471765
0.9029	High Similarity	NPC469916
0.9029	High Similarity	NPC472439
0.8969	High Similarity	NPC472416
0.8969	High Similarity	NPC472360
0.8866	High Similarity	NPC99653
0.8788	High Similarity	NPC202833
0.8776	High Similarity	NPC182826
0.8776	High Similarity	NPC105375
0.8763	High Similarity	NPC124374
0.8762	High Similarity	NPC475586
0.875	High Similarity	NPC67321
0.875	High Similarity	NPC187435
0.875	High Similarity	NPC112780
0.8725	High Similarity	NPC295791
0.87	High Similarity	NPC473244
0.8687	High Similarity	NPC471786
0.8687	High Similarity	NPC37603
0.8667	High Similarity	NPC476479
0.866	High Similarity	NPC48732
0.866	High Similarity	NPC220216
0.8641	High Similarity	NPC159533
0.8611	High Similarity	NPC471204
0.86	High Similarity	NPC129569
0.8585	High Similarity	NPC273433
0.8557	High Similarity	NPC261320
0.8544	High Similarity	NPC472552
0.8544	High Similarity	NPC476081
0.8519	High Similarity	NPC317687
0.8491	Intermediate Similarity	NPC306265
0.8476	Intermediate Similarity	NPC472389
0.8454	Intermediate Similarity	NPC69713
0.8447	Intermediate Similarity	NPC472554
0.8431	Intermediate Similarity	NPC216478
0.8426	Intermediate Similarity	NPC317107
0.8396	Intermediate Similarity	NPC472390
0.8384	Intermediate Similarity	NPC473944
0.8378	Intermediate Similarity	NPC473968
0.8367	Intermediate Similarity	NPC246028
0.8365	Intermediate Similarity	NPC165250
0.8351	Intermediate Similarity	NPC471779
0.8351	Intermediate Similarity	NPC102640
0.835	Intermediate Similarity	NPC47024
0.835	Intermediate Similarity	NPC38855
0.835	Intermediate Similarity	NPC188968
0.835	Intermediate Similarity	NPC79303
0.8333	Intermediate Similarity	NPC474395
0.8318	Intermediate Similarity	NPC322903
0.8302	Intermediate Similarity	NPC284365
0.8302	Intermediate Similarity	NPC123726
0.8288	Intermediate Similarity	NPC234858
0.8288	Intermediate Similarity	NPC471127
0.8288	Intermediate Similarity	NPC154363
0.8286	Intermediate Similarity	NPC120321
0.8286	Intermediate Similarity	NPC95899
0.8286	Intermediate Similarity	NPC478057
0.8273	Intermediate Similarity	NPC25909
0.8252	Intermediate Similarity	NPC222303
0.8247	Intermediate Similarity	NPC102996
0.8241	Intermediate Similarity	NPC284828
0.8241	Intermediate Similarity	NPC5475
0.8241	Intermediate Similarity	NPC173905
0.8241	Intermediate Similarity	NPC472216
0.8235	Intermediate Similarity	NPC234993
0.8235	Intermediate Similarity	NPC165632
0.8235	Intermediate Similarity	NPC134072
0.823	Intermediate Similarity	NPC476529
0.823	Intermediate Similarity	NPC475775
0.8224	Intermediate Similarity	NPC473586
0.8214	Intermediate Similarity	NPC469684
0.8214	Intermediate Similarity	NPC10721
0.8208	Intermediate Similarity	NPC146731
0.8208	Intermediate Similarity	NPC118911
0.8208	Intermediate Similarity	NPC65523
0.8208	Intermediate Similarity	NPC296950
0.8198	Intermediate Similarity	NPC181145
0.819	Intermediate Similarity	NPC469606
0.819	Intermediate Similarity	NPC273005
0.819	Intermediate Similarity	NPC31058
0.8182	Intermediate Similarity	NPC269530
0.8182	Intermediate Similarity	NPC472002
0.8182	Intermediate Similarity	NPC314727
0.8174	Intermediate Similarity	NPC23786
0.8174	Intermediate Similarity	NPC470265
0.8173	Intermediate Similarity	NPC271295
0.8165	Intermediate Similarity	NPC472215
0.8165	Intermediate Similarity	NPC469917
0.8165	Intermediate Similarity	NPC83005
0.8165	Intermediate Similarity	NPC472214
0.8165	Intermediate Similarity	NPC5103
0.8165	Intermediate Similarity	NPC472417
0.8158	Intermediate Similarity	NPC471128
0.8158	Intermediate Similarity	NPC107338
0.8158	Intermediate Similarity	NPC48692
0.8158	Intermediate Similarity	NPC157252
0.8158	Intermediate Similarity	NPC109607
0.8158	Intermediate Similarity	NPC471126
0.8158	Intermediate Similarity	NPC145182
0.8155	Intermediate Similarity	NPC91695
0.8155	Intermediate Similarity	NPC254496
0.8155	Intermediate Similarity	NPC287668
0.8155	Intermediate Similarity	NPC320306
0.8155	Intermediate Similarity	NPC70145
0.8155	Intermediate Similarity	NPC285513
0.8148	Intermediate Similarity	NPC325054
0.8148	Intermediate Similarity	NPC472218
0.8148	Intermediate Similarity	NPC293850
0.8148	Intermediate Similarity	NPC88701
0.8148	Intermediate Similarity	NPC275539
0.8148	Intermediate Similarity	NPC472217
0.8148	Intermediate Similarity	NPC472219
0.8148	Intermediate Similarity	NPC475263
0.8148	Intermediate Similarity	NPC189075
0.8142	Intermediate Similarity	NPC251310
0.8137	Intermediate Similarity	NPC157686
0.8137	Intermediate Similarity	NPC259042
0.8137	Intermediate Similarity	NPC276110
0.8131	Intermediate Similarity	NPC34768
0.8131	Intermediate Similarity	NPC469607
0.8113	Intermediate Similarity	NPC23584
0.8113	Intermediate Similarity	NPC61442
0.8113	Intermediate Similarity	NPC471208
0.8108	Intermediate Similarity	NPC469463
0.8108	Intermediate Similarity	NPC469454
0.8108	Intermediate Similarity	NPC472757
0.8108	Intermediate Similarity	NPC75167
0.8108	Intermediate Similarity	NPC469496
0.8108	Intermediate Similarity	NPC311592
0.8103	Intermediate Similarity	NPC67251
0.81	Intermediate Similarity	NPC232202
0.81	Intermediate Similarity	NPC473099
0.8095	Intermediate Similarity	NPC303559
0.8095	Intermediate Similarity	NPC471412
0.8095	Intermediate Similarity	NPC111292
0.8091	Intermediate Similarity	NPC475668
0.8091	Intermediate Similarity	NPC188738
0.8091	Intermediate Similarity	NPC469656
0.8091	Intermediate Similarity	NPC475480
0.8091	Intermediate Similarity	NPC324683
0.8091	Intermediate Similarity	NPC474846
0.8091	Intermediate Similarity	NPC473921
0.8091	Intermediate Similarity	NPC469655
0.8087	Intermediate Similarity	NPC67569
0.8087	Intermediate Similarity	NPC52839
0.8077	Intermediate Similarity	NPC478056
0.8077	Intermediate Similarity	NPC316598
0.8073	Intermediate Similarity	NPC474243
0.8073	Intermediate Similarity	NPC42662
0.8073	Intermediate Similarity	NPC31522
0.8073	Intermediate Similarity	NPC299590
0.807	Intermediate Similarity	NPC77689
0.807	Intermediate Similarity	NPC475041
0.807	Intermediate Similarity	NPC473636
0.807	Intermediate Similarity	NPC236918
0.807	Intermediate Similarity	NPC156745
0.807	Intermediate Similarity	NPC469380
0.8061	Intermediate Similarity	NPC473226
0.8058	Intermediate Similarity	NPC7124
0.8058	Intermediate Similarity	NPC472995
0.8058	Intermediate Similarity	NPC284518
0.8056	Intermediate Similarity	NPC471205
0.8056	Intermediate Similarity	NPC110496
0.8056	Intermediate Similarity	NPC184512
0.8056	Intermediate Similarity	NPC230541
0.8053	Intermediate Similarity	NPC473590
0.8053	Intermediate Similarity	NPC134430
0.8053	Intermediate Similarity	NPC53396
0.8053	Intermediate Similarity	NPC98249
0.8039	Intermediate Similarity	NPC469596
0.8039	Intermediate Similarity	NPC24861
0.8039	Intermediate Similarity	NPC225474
0.8039	Intermediate Similarity	NPC148000
0.8037	Intermediate Similarity	NPC258532
0.8037	Intermediate Similarity	NPC473543
0.8036	Intermediate Similarity	NPC472400
0.8036	Intermediate Similarity	NPC473798
0.8034	Intermediate Similarity	NPC476729
0.8034	Intermediate Similarity	NPC470922
0.802	Intermediate Similarity	NPC477574
0.8019	Intermediate Similarity	NPC155332
0.8019	Intermediate Similarity	NPC32577
0.8019	Intermediate Similarity	NPC58329
0.8019	Intermediate Similarity	NPC475038
0.8019	Intermediate Similarity	NPC475344
0.8019	Intermediate Similarity	NPC11956
0.8019	Intermediate Similarity	NPC109195
0.8019	Intermediate Similarity	NPC476471
0.8019	Intermediate Similarity	NPC162973
0.8019	Intermediate Similarity	NPC114540
0.8019	Intermediate Similarity	NPC474709
0.8018	Intermediate Similarity	NPC474516

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 NPC111952 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	1741
0.2-0.3	3528
0.3-0.4	2291
0.4-0.5	909
0.5-0.6	301
0.6-0.7	164
0.7-0.8	13
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
0.8073	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7639	Approved
0.8	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD7638	Approved
0.7818	Intermediate Similarity	NPD6686	Approved
0.7745	Intermediate Similarity	NPD6698	Approved
0.7745	Intermediate Similarity	NPD46	Approved
0.7739	Intermediate Similarity	NPD7115	Discovery
0.7736	Intermediate Similarity	NPD4225	Approved
0.7727	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5344	Discontinued
0.7524	Intermediate Similarity	NPD7748	Approved
0.7523	Intermediate Similarity	NPD7632	Discontinued
0.75	Intermediate Similarity	NPD7515	Phase 2
0.7477	Intermediate Similarity	NPD7902	Approved
0.7434	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8297	Approved
0.7377	Intermediate Similarity	NPD7507	Approved
0.7345	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6648	Approved
0.7339	Intermediate Similarity	NPD7319	Approved
0.7321	Intermediate Similarity	NPD6402	Approved
0.7321	Intermediate Similarity	NPD7128	Approved
0.7321	Intermediate Similarity	NPD5739	Approved
0.7321	Intermediate Similarity	NPD6675	Approved
0.7281	Intermediate Similarity	NPD6372	Approved
0.7281	Intermediate Similarity	NPD6373	Approved
0.7264	Intermediate Similarity	NPD5778	Approved
0.7264	Intermediate Similarity	NPD5779	Approved
0.7264	Intermediate Similarity	NPD6399	Phase 3
0.7257	Intermediate Similarity	NPD6412	Phase 2
0.725	Intermediate Similarity	NPD6319	Approved
0.7227	Intermediate Similarity	NPD7327	Approved
0.7227	Intermediate Similarity	NPD7328	Approved
0.7217	Intermediate Similarity	NPD6371	Approved
0.7213	Intermediate Similarity	NPD8328	Phase 3
0.7196	Intermediate Similarity	NPD7900	Approved
0.7196	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7320	Approved
0.7193	Intermediate Similarity	NPD6899	Approved
0.7193	Intermediate Similarity	NPD6881	Approved
0.7179	Intermediate Similarity	NPD4632	Approved
0.7167	Intermediate Similarity	NPD7516	Approved
0.7155	Intermediate Similarity	NPD6650	Approved
0.7155	Intermediate Similarity	NPD6649	Approved
0.7105	Intermediate Similarity	NPD5697	Approved
0.7105	Intermediate Similarity	NPD5701	Approved
0.7094	Intermediate Similarity	NPD6882	Approved
0.7094	Intermediate Similarity	NPD6053	Discontinued
0.7087	Intermediate Similarity	NPD1694	Approved
0.7075	Intermediate Similarity	NPD7838	Discovery
0.7069	Intermediate Similarity	NPD6883	Approved
0.7069	Intermediate Similarity	NPD7102	Approved
0.7069	Intermediate Similarity	NPD7290	Approved
0.7049	Intermediate Similarity	NPD8296	Approved
0.7049	Intermediate Similarity	NPD8033	Approved
0.7049	Intermediate Similarity	NPD8380	Approved
0.7049	Intermediate Similarity	NPD8335	Approved
0.7049	Intermediate Similarity	NPD8378	Approved
0.7049	Intermediate Similarity	NPD8379	Approved
0.7034	Intermediate Similarity	NPD8133	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.7018	Intermediate Similarity	NPD6008	Approved
0.7016	Intermediate Similarity	NPD7492	Approved
0.7009	Intermediate Similarity	NPD7983	Approved
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.7	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6012	Approved
0.6983	Remote Similarity	NPD6014	Approved
0.6983	Remote Similarity	NPD6013	Approved
0.6981	Remote Similarity	NPD5328	Approved
0.6967	Remote Similarity	NPD6059	Approved
0.6967	Remote Similarity	NPD8377	Approved
0.6967	Remote Similarity	NPD6054	Approved
0.6967	Remote Similarity	NPD8294	Approved
0.6961	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6616	Approved
0.6937	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7604	Phase 2
0.6911	Remote Similarity	NPD8515	Approved
0.6911	Remote Similarity	NPD8517	Approved
0.6911	Remote Similarity	NPD7503	Approved
0.6911	Remote Similarity	NPD8516	Approved
0.6911	Remote Similarity	NPD5983	Phase 2
0.6911	Remote Similarity	NPD8513	Phase 3
0.6905	Remote Similarity	NPD8293	Discontinued
0.6905	Remote Similarity	NPD7078	Approved
0.6903	Remote Similarity	NPD5211	Phase 2
0.6897	Remote Similarity	NPD6011	Approved
0.6864	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7334	Approved
0.6857	Remote Similarity	NPD6409	Approved
0.6857	Remote Similarity	NPD6684	Approved
0.6857	Remote Similarity	NPD7146	Approved
0.6857	Remote Similarity	NPD7521	Approved
0.6857	Remote Similarity	NPD5330	Approved
0.6855	Remote Similarity	NPD6370	Approved
0.6852	Remote Similarity	NPD7637	Suspended
0.6852	Remote Similarity	NPD6411	Approved
0.6852	Remote Similarity	NPD6079	Approved
0.685	Remote Similarity	NPD7736	Approved
0.6847	Remote Similarity	NPD4755	Approved
0.6827	Remote Similarity	NPD4786	Approved
0.6825	Remote Similarity	NPD6336	Discontinued
0.6822	Remote Similarity	NPD7260	Phase 2
0.6818	Remote Similarity	NPD5695	Phase 3
0.681	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3667	Approved
0.6789	Remote Similarity	NPD4202	Approved
0.6783	Remote Similarity	NPD5141	Approved
0.6774	Remote Similarity	NPD6016	Approved
0.6774	Remote Similarity	NPD6015	Approved
0.6774	Remote Similarity	NPD6921	Approved
0.6759	Remote Similarity	NPD5785	Approved
0.6729	Remote Similarity	NPD6903	Approved
0.6729	Remote Similarity	NPD6672	Approved
0.6729	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5737	Approved
0.6726	Remote Similarity	NPD4700	Approved
0.6726	Remote Similarity	NPD5286	Approved
0.6726	Remote Similarity	NPD4696	Approved
0.6726	Remote Similarity	NPD5285	Approved
0.6723	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5988	Approved
0.6697	Remote Similarity	NPD8035	Phase 2
0.6697	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6641	Remote Similarity	NPD6845	Suspended
0.6641	Remote Similarity	NPD8074	Phase 3
0.6639	Remote Similarity	NPD4634	Approved
0.6639	Remote Similarity	NPD6274	Approved
0.6637	Remote Similarity	NPD5696	Approved
0.6636	Remote Similarity	NPD3573	Approved
0.6613	Remote Similarity	NPD7100	Approved
0.6613	Remote Similarity	NPD7101	Approved
0.6609	Remote Similarity	NPD5225	Approved
0.6609	Remote Similarity	NPD5224	Approved
0.6609	Remote Similarity	NPD5226	Approved
0.6609	Remote Similarity	NPD4633	Approved
0.6607	Remote Similarity	NPD4697	Phase 3
0.6607	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5221	Approved
0.6607	Remote Similarity	NPD5222	Approved
0.6604	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4767	Approved
0.6581	Remote Similarity	NPD4768	Approved
0.6552	Remote Similarity	NPD5174	Approved
0.6552	Remote Similarity	NPD5175	Approved
0.6549	Remote Similarity	NPD5173	Approved
0.6545	Remote Similarity	NPD5693	Phase 1
0.6532	Remote Similarity	NPD6335	Approved
0.6522	Remote Similarity	NPD5223	Approved
0.6518	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4753	Phase 2
0.6514	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6909	Approved
0.6508	Remote Similarity	NPD6908	Approved
0.6504	Remote Similarity	NPD6868	Approved
0.6481	Remote Similarity	NPD7524	Approved
0.6471	Remote Similarity	NPD4729	Approved
0.6471	Remote Similarity	NPD4730	Approved
0.6462	Remote Similarity	NPD6033	Approved
0.6452	Remote Similarity	NPD6317	Approved
0.6442	Remote Similarity	NPD4695	Discontinued
0.6429	Remote Similarity	NPD5282	Discontinued
0.6415	Remote Similarity	NPD6695	Phase 3
0.6415	Remote Similarity	NPD7154	Phase 3
0.641	Remote Similarity	NPD4754	Approved
0.6408	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6313	Approved
0.64	Remote Similarity	NPD6314	Approved
0.6396	Remote Similarity	NPD5281	Approved
0.6396	Remote Similarity	NPD5284	Approved
0.6389	Remote Similarity	NPD5279	Phase 3
0.6389	Remote Similarity	NPD4623	Approved
0.6389	Remote Similarity	NPD4519	Discontinued
0.6364	Remote Similarity	NPD5247	Approved
0.6364	Remote Similarity	NPD5248	Approved
0.6364	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD6904	Approved
0.6364	Remote Similarity	NPD5250	Approved
0.6364	Remote Similarity	NPD6080	Approved
0.6364	Remote Similarity	NPD5249	Phase 3
0.6364	Remote Similarity	NPD5251	Approved
0.6355	Remote Similarity	NPD3668	Phase 3

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