NPASS Compound

Structure

NPC236918 OpenBabel07101718272D 37 40 0 0 1 0 0 0 0 0999 V2000 3.5086 2.9478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2521 -1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9033 2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 -1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6501 3.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7767 2.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9183 3.4867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0449 2.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8136 3.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6870 3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4921 -0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4412 -3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7541 -2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0938 -4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3011 -1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4452 -3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -2.2764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7019 2.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9921 -2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1073 -4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7468 0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5753 1.5387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5799 -3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3265 -1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 24 1 0 0 0 0 13 17 2 0 0 0 0 13 22 1 0 0 0 0 14 20 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 31 1 0 0 0 0 17 25 1 0 0 0 0 18 27 1 0 0 0 0 18 29 1 6 0 0 0 19 32 2 0 0 0 0 19 37 1 0 0 0 0 21 14 1 1 0 0 0 21 22 1 0 0 0 0 21 25 1 0 0 0 0 22 29 1 1 0 0 0 23 26 1 0 0 0 0 23 29 1 6 0 0 0 24 33 2 0 0 0 0 24 36 1 0 0 0 0 25 34 2 0 0 0 0 26 28 1 0 0 0 0 26 30 1 1 0 0 0 27 30 1 1 0 0 0 27 36 1 0 0 0 0 28 30 1 0 0 0 0 29 35 1 6 0 0 0 30 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.28
Volume:	536.287
LogP:	3.915
LogD:	2.933
LogS:	-4.644
# Rotatable Bonds:	9
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	5.407
Fsp3:	0.633
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:	-4.777
MDCK Permeability:	1.4274849490902852e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.387
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.249

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.672
Plasma Protein Binding (PPB):	73.8860092163086%
Volume Distribution (VD):	0.828
Pgp-substrate:	20.36231231689453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.327
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.771
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	2.638
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.789
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.444
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.814
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.925
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC236918

Natural Product ID:	NPC236918
*Common Name:**	Pedilstatin
IUPAC Name:	n.a.
Synonyms:	pedilstatin
Standard InCHIKey:	ALKHEZOKTHCOBM-GTBZSHDQSA-N
Standard InCHI:	InChI=1S/C30H40O7/c1-7-8-9-10-11-12-24(33)36-27-18(3)29(35)22-13-17(2)25(34)21(22)14-20(16-31)15-23(29)26-28(5,6)30(26,27)37-19(4)32/h9-13,15,18,21-23,26-27,31,35H,7-8,14,16H2,1-6H3/b10-9+,12-11-/t18-,21-,22-,23+,26-,27-,29+,30-/m1/s1
SMILES:	CCC/C=C/C=CC(=O)O[C@@H]1[C@@H](C)[C@]2(O)[C@@H]3C=C(C(=O)[C@@H]3CC(=C[C@H]2[C@H]2[C@]1(OC(=O)C)C2(C)C)CO)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519593
PubChem CID:	643665
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO32922	pedilanthus sp.	Species	Euphorbiaceae	Eukaryota	n.a.	maldives	n.a.	PMID[12350143]

☑ 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
EC50	1
ED50	1
IC50	1
Ki	1
Others	1

Activity Type	# Activity
Cell Line	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.28	ug ml-1	PMID[530076]
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	13300.0	nM	PMID[530076]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	80.0	%	PMID[530076]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	1030.0	nM	PMID[530076]
NPT2	Others	Unspecified		Ki	=	620.0	nM	PMID[530076]

☑ 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 NPC236918 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	238
0.1-0.2	1267
0.2-0.3	3826
0.3-0.4	6303
0.4-0.5	13170
0.5-0.6	10155
0.6-0.7	6125
0.7-0.8	1402
0.8-0.85	93
0.85-0.9	48
0.9-0.95	42
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC156745
0.9909	High Similarity	NPC472759
0.9909	High Similarity	NPC329080
0.9909	High Similarity	NPC475885
0.9725	High Similarity	NPC234858
0.9725	High Similarity	NPC154363
0.9725	High Similarity	NPC471127
0.9636	High Similarity	NPC10721
0.9561	High Similarity	NPC145238
0.955	High Similarity	NPC124676
0.955	High Similarity	NPC146280
0.9541	High Similarity	NPC472757
0.9455	High Similarity	NPC472400
0.9381	High Similarity	NPC471126
0.9381	High Similarity	NPC471128
0.9381	High Similarity	NPC145182
0.9381	High Similarity	NPC157252
0.9298	High Similarity	NPC52839
0.9217	High Similarity	NPC257017
0.9217	High Similarity	NPC162009
0.9211	High Similarity	NPC19336
0.9211	High Similarity	NPC185876
0.9204	High Similarity	NPC171905
0.9204	High Similarity	NPC472758
0.9204	High Similarity	NPC471125
0.9204	High Similarity	NPC472760
0.9204	High Similarity	NPC472397
0.9138	High Similarity	NPC472399
0.9123	High Similarity	NPC5989
0.9123	High Similarity	NPC471108
0.9123	High Similarity	NPC255081
0.9123	High Similarity	NPC5991
0.9123	High Similarity	NPC180640
0.9123	High Similarity	NPC275696
0.9123	High Similarity	NPC22628
0.9115	High Similarity	NPC156252
0.9018	High Similarity	NPC71889
0.8966	High Similarity	NPC472401
0.8947	High Similarity	NPC153651
0.8938	High Similarity	NPC474872
0.8889	High Similarity	NPC19464
0.8839	High Similarity	NPC475937
0.8839	High Similarity	NPC174471
0.8839	High Similarity	NPC158523
0.8839	High Similarity	NPC260786
0.8839	High Similarity	NPC474871
0.8839	High Similarity	NPC96739
0.8761	High Similarity	NPC170212
0.8761	High Similarity	NPC221511
0.8761	High Similarity	NPC265499
0.8761	High Similarity	NPC17138
0.8761	High Similarity	NPC89227
0.8761	High Similarity	NPC101825
0.8761	High Similarity	NPC151216
0.8761	High Similarity	NPC215643
0.8761	High Similarity	NPC475391
0.875	High Similarity	NPC153036
0.875	High Similarity	NPC471940
0.8684	High Similarity	NPC474937
0.8678	High Similarity	NPC236999
0.8678	High Similarity	NPC270109
0.8667	High Similarity	NPC471939
0.8632	High Similarity	NPC472667
0.8583	High Similarity	NPC473709
0.8583	High Similarity	NPC473919
0.8548	High Similarity	NPC476111
0.8512	High Similarity	NPC222307
0.85	High Similarity	NPC473802
0.8496	Intermediate Similarity	NPC163004
0.8496	Intermediate Similarity	NPC273433
0.8403	Intermediate Similarity	NPC143755
0.8362	Intermediate Similarity	NPC469463
0.8362	Intermediate Similarity	NPC469496
0.8362	Intermediate Similarity	NPC469454
0.8362	Intermediate Similarity	NPC46269
0.8362	Intermediate Similarity	NPC477091
0.8362	Intermediate Similarity	NPC106395
0.8361	Intermediate Similarity	NPC293112
0.8333	Intermediate Similarity	NPC310511
0.832	Intermediate Similarity	NPC90814
0.832	Intermediate Similarity	NPC189393
0.8319	Intermediate Similarity	NPC470186
0.8319	Intermediate Similarity	NPC67321
0.8319	Intermediate Similarity	NPC187435
0.8305	Intermediate Similarity	NPC469684
0.8291	Intermediate Similarity	NPC67290
0.8291	Intermediate Similarity	NPC138303
0.8291	Intermediate Similarity	NPC133677
0.8276	Intermediate Similarity	NPC76550
0.8276	Intermediate Similarity	NPC123855
0.8276	Intermediate Similarity	NPC138757
0.825	Intermediate Similarity	NPC475003
0.8235	Intermediate Similarity	NPC284707
0.8226	Intermediate Similarity	NPC470850
0.822	Intermediate Similarity	NPC470793
0.822	Intermediate Similarity	NPC179626
0.8205	Intermediate Similarity	NPC471204
0.8197	Intermediate Similarity	NPC469789
0.8197	Intermediate Similarity	NPC11895
0.8195	Intermediate Similarity	NPC140021
0.819	Intermediate Similarity	NPC474846
0.819	Intermediate Similarity	NPC304180
0.819	Intermediate Similarity	NPC469655
0.819	Intermediate Similarity	NPC469656
0.819	Intermediate Similarity	NPC179798
0.8189	Intermediate Similarity	NPC100017
0.8189	Intermediate Similarity	NPC182266
0.8189	Intermediate Similarity	NPC471137
0.8189	Intermediate Similarity	NPC475500
0.8189	Intermediate Similarity	NPC223356
0.8189	Intermediate Similarity	NPC473548
0.8189	Intermediate Similarity	NPC471136
0.8189	Intermediate Similarity	NPC475154
0.8182	Intermediate Similarity	NPC67569
0.816	Intermediate Similarity	NPC104382
0.816	Intermediate Similarity	NPC470851
0.8158	Intermediate Similarity	NPC143609
0.8151	Intermediate Similarity	NPC98249
0.8151	Intermediate Similarity	NPC53396
0.8151	Intermediate Similarity	NPC474518
0.8136	Intermediate Similarity	NPC73314
0.813	Intermediate Similarity	NPC81736
0.813	Intermediate Similarity	NPC172154
0.8125	Intermediate Similarity	NPC476081
0.8125	Intermediate Similarity	NPC478156
0.812	Intermediate Similarity	NPC472002
0.8115	Intermediate Similarity	NPC470265
0.8115	Intermediate Similarity	NPC23786
0.8115	Intermediate Similarity	NPC170538
0.8103	Intermediate Similarity	NPC253906
0.8103	Intermediate Similarity	NPC257240
0.8103	Intermediate Similarity	NPC5103
0.8099	Intermediate Similarity	NPC4548
0.8095	Intermediate Similarity	NPC477189
0.8095	Intermediate Similarity	NPC251564
0.8095	Intermediate Similarity	NPC475606
0.8095	Intermediate Similarity	NPC475314
0.8087	Intermediate Similarity	NPC306265
0.8087	Intermediate Similarity	NPC102843
0.807	Intermediate Similarity	NPC34768
0.807	Intermediate Similarity	NPC111952
0.8067	Intermediate Similarity	NPC471816
0.8067	Intermediate Similarity	NPC176840
0.8065	Intermediate Similarity	NPC473635
0.8062	Intermediate Similarity	NPC68282
0.8062	Intermediate Similarity	NPC243902
0.8053	Intermediate Similarity	NPC23584
0.8051	Intermediate Similarity	NPC474271
0.8051	Intermediate Similarity	NPC56448
0.8051	Intermediate Similarity	NPC25909
0.8049	Intermediate Similarity	NPC473979
0.8034	Intermediate Similarity	NPC188738
0.8034	Intermediate Similarity	NPC470076
0.8031	Intermediate Similarity	NPC474508
0.8031	Intermediate Similarity	NPC473485
0.8031	Intermediate Similarity	NPC475139
0.8031	Intermediate Similarity	NPC180902
0.8017	Intermediate Similarity	NPC475041
0.8017	Intermediate Similarity	NPC228477
0.8017	Intermediate Similarity	NPC137911
0.8017	Intermediate Similarity	NPC47951
0.8017	Intermediate Similarity	NPC469380
0.8017	Intermediate Similarity	NPC469370
0.8016	Intermediate Similarity	NPC231529
0.8016	Intermediate Similarity	NPC175186
0.8	Intermediate Similarity	NPC475323
0.8	Intermediate Similarity	NPC284068
0.8	Intermediate Similarity	NPC470493
0.8	Intermediate Similarity	NPC473656
0.8	Intermediate Similarity	NPC284518
0.8	Intermediate Similarity	NPC23046
0.8	Intermediate Similarity	NPC183580
0.8	Intermediate Similarity	NPC312824
0.7984	Intermediate Similarity	NPC8369
0.7983	Intermediate Similarity	NPC238667
0.7982	Intermediate Similarity	NPC118911
0.7982	Intermediate Similarity	NPC239162
0.7966	Intermediate Similarity	NPC470063
0.7966	Intermediate Similarity	NPC269530
0.7966	Intermediate Similarity	NPC236217
0.7966	Intermediate Similarity	NPC234042
0.7966	Intermediate Similarity	NPC152117
0.7966	Intermediate Similarity	NPC476801
0.7965	Intermediate Similarity	NPC11956
0.7965	Intermediate Similarity	NPC137430
0.7965	Intermediate Similarity	NPC162973
0.7953	Intermediate Similarity	NPC471170
0.7951	Intermediate Similarity	NPC268530
0.7951	Intermediate Similarity	NPC48692
0.7951	Intermediate Similarity	NPC476962
0.7951	Intermediate Similarity	NPC154491
0.7949	Intermediate Similarity	NPC477103
0.7949	Intermediate Similarity	NPC472214
0.7949	Intermediate Similarity	NPC472215
0.7946	Intermediate Similarity	NPC474718
0.7946	Intermediate Similarity	NPC470074
0.7946	Intermediate Similarity	NPC47024
0.7934	Intermediate Similarity	NPC186525
0.7934	Intermediate Similarity	NPC50774
0.7934	Intermediate Similarity	NPC108581

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 NPC236918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1516
0.2-0.3	3484
0.3-0.4	2459
0.4-0.5	963
0.5-0.6	356
0.6-0.7	151
0.7-0.8	10
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8103	Intermediate Similarity	NPD6371	Approved
0.7946	Intermediate Similarity	NPD6648	Approved
0.7876	Intermediate Similarity	NPD5344	Discontinued
0.7851	Intermediate Similarity	NPD7115	Discovery
0.7712	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4225	Approved
0.7328	Intermediate Similarity	NPD7639	Approved
0.7328	Intermediate Similarity	NPD7640	Approved
0.7241	Intermediate Similarity	NPD7638	Approved
0.7236	Intermediate Similarity	NPD8297	Approved
0.7209	Intermediate Similarity	NPD7604	Phase 2
0.719	Intermediate Similarity	NPD6881	Approved
0.719	Intermediate Similarity	NPD6686	Approved
0.719	Intermediate Similarity	NPD6899	Approved
0.7177	Intermediate Similarity	NPD4632	Approved
0.7154	Intermediate Similarity	NPD6650	Approved
0.7154	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6319	Approved
0.7107	Intermediate Similarity	NPD5697	Approved
0.7099	Intermediate Similarity	NPD7507	Approved
0.708	Intermediate Similarity	NPD46	Approved
0.708	Intermediate Similarity	NPD7838	Discovery
0.708	Intermediate Similarity	NPD6698	Approved
0.7073	Intermediate Similarity	NPD7102	Approved
0.7073	Intermediate Similarity	NPD6883	Approved
0.7073	Intermediate Similarity	NPD7290	Approved
0.7068	Intermediate Similarity	NPD7319	Approved
0.7031	Intermediate Similarity	NPD7516	Approved
0.7025	Intermediate Similarity	NPD7128	Approved
0.7025	Intermediate Similarity	NPD6008	Approved
0.7025	Intermediate Similarity	NPD5739	Approved
0.7025	Intermediate Similarity	NPD6675	Approved
0.7025	Intermediate Similarity	NPD6402	Approved
0.7023	Intermediate Similarity	NPD7492	Approved
0.7016	Intermediate Similarity	NPD8130	Phase 1
0.7016	Intermediate Similarity	NPD6847	Approved
0.7016	Intermediate Similarity	NPD6617	Approved
0.7016	Intermediate Similarity	NPD6869	Approved
0.7008	Intermediate Similarity	NPD6009	Approved
0.6992	Remote Similarity	NPD6014	Approved
0.6992	Remote Similarity	NPD6013	Approved
0.6992	Remote Similarity	NPD6372	Approved
0.6992	Remote Similarity	NPD6373	Approved
0.6992	Remote Similarity	NPD6012	Approved
0.6977	Remote Similarity	NPD6054	Approved
0.697	Remote Similarity	NPD6616	Approved
0.6967	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6882	Approved
0.696	Remote Similarity	NPD6053	Discontinued
0.6957	Remote Similarity	NPD5779	Approved
0.6957	Remote Similarity	NPD5778	Approved
0.6953	Remote Similarity	NPD7327	Approved
0.6953	Remote Similarity	NPD7328	Approved
0.6949	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7503	Approved
0.6923	Remote Similarity	NPD5983	Phase 2
0.6923	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD8517	Approved
0.6923	Remote Similarity	NPD8515	Approved
0.6917	Remote Similarity	NPD5211	Phase 2
0.6917	Remote Similarity	NPD7078	Approved
0.6911	Remote Similarity	NPD6011	Approved
0.6911	Remote Similarity	NPD7320	Approved
0.687	Remote Similarity	NPD7637	Suspended
0.687	Remote Similarity	NPD7983	Approved
0.687	Remote Similarity	NPD6370	Approved
0.6866	Remote Similarity	NPD7736	Approved
0.6842	Remote Similarity	NPD6336	Discontinued
0.6838	Remote Similarity	NPD7260	Phase 2
0.6829	Remote Similarity	NPD5701	Approved
0.681	Remote Similarity	NPD6399	Phase 3
0.6803	Remote Similarity	NPD5141	Approved
0.6794	Remote Similarity	NPD6015	Approved
0.6794	Remote Similarity	NPD6016	Approved
0.6794	Remote Similarity	NPD6921	Approved
0.6786	Remote Similarity	NPD1694	Approved
0.6786	Remote Similarity	NPD1696	Phase 3
0.6783	Remote Similarity	NPD5785	Approved
0.6777	Remote Similarity	NPD7632	Discontinued
0.675	Remote Similarity	NPD5285	Approved
0.675	Remote Similarity	NPD5286	Approved
0.675	Remote Similarity	NPD4696	Approved
0.6742	Remote Similarity	NPD5988	Approved
0.6724	Remote Similarity	NPD6079	Approved
0.6723	Remote Similarity	NPD7902	Approved
0.6718	Remote Similarity	NPD6059	Approved
0.6696	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6641	Remote Similarity	NPD7101	Approved
0.6641	Remote Similarity	NPD7100	Approved
0.6639	Remote Similarity	NPD4633	Approved
0.6639	Remote Similarity	NPD5226	Approved
0.6639	Remote Similarity	NPD5224	Approved
0.6639	Remote Similarity	NPD5225	Approved
0.6614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7748	Approved
0.661	Remote Similarity	NPD5282	Discontinued
0.6591	Remote Similarity	NPD8377	Approved
0.6591	Remote Similarity	NPD8294	Approved
0.6587	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5174	Approved
0.6585	Remote Similarity	NPD5175	Approved
0.6583	Remote Similarity	NPD6083	Phase 2
0.6583	Remote Similarity	NPD6084	Phase 2
0.6583	Remote Similarity	NPD4755	Approved
0.6581	Remote Similarity	NPD6411	Approved
0.6581	Remote Similarity	NPD5281	Approved
0.6581	Remote Similarity	NPD5284	Approved
0.6581	Remote Similarity	NPD7515	Phase 2
0.6567	Remote Similarity	NPD8328	Phase 3
0.6565	Remote Similarity	NPD6335	Approved
0.656	Remote Similarity	NPD6412	Phase 2
0.6557	Remote Similarity	NPD5223	Approved
0.6555	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5328	Approved
0.6549	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6274	Approved
0.6518	Remote Similarity	NPD5209	Approved
0.6518	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8133	Approved
0.65	Remote Similarity	NPD5221	Approved
0.65	Remote Similarity	NPD5222	Approved
0.65	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6317	Approved
0.6484	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD7900	Approved
0.6471	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6695	Phase 3
0.6446	Remote Similarity	NPD5173	Approved
0.6439	Remote Similarity	NPD6314	Approved
0.6439	Remote Similarity	NPD6313	Approved
0.6435	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD6845	Suspended
0.6418	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5695	Phase 3
0.6412	Remote Similarity	NPD6868	Approved
0.641	Remote Similarity	NPD6101	Approved
0.641	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5696	Approved
0.6387	Remote Similarity	NPD4202	Approved
0.6379	Remote Similarity	NPD3573	Approved
0.6378	Remote Similarity	NPD4729	Approved
0.6378	Remote Similarity	NPD4730	Approved
0.6364	Remote Similarity	NPD4697	Phase 3
0.6348	Remote Similarity	NPD5363	Approved
0.6339	Remote Similarity	NPD7332	Phase 2
0.6316	Remote Similarity	NPD7154	Phase 3
0.6316	Remote Similarity	NPD5362	Discontinued
0.6306	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8034	Phase 2
0.6303	Remote Similarity	NPD8035	Phase 2
0.6296	Remote Similarity	NPD6908	Approved
0.6296	Remote Similarity	NPD6909	Approved
0.6283	Remote Similarity	NPD6902	Approved
0.6281	Remote Similarity	NPD5210	Approved
0.6281	Remote Similarity	NPD4629	Approved
0.6279	Remote Similarity	NPD5250	Approved
0.6279	Remote Similarity	NPD5249	Phase 3
0.6279	Remote Similarity	NPD5247	Approved
0.6279	Remote Similarity	NPD5251	Approved
0.6279	Remote Similarity	NPD5248	Approved
0.6261	Remote Similarity	NPD4786	Approved
0.6259	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD5128	Approved
0.6241	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7750	Discontinued
0.6231	Remote Similarity	NPD5215	Approved
0.6231	Remote Similarity	NPD5216	Approved
0.6231	Remote Similarity	NPD5217	Approved
0.623	Remote Similarity	NPD7839	Suspended
0.6225	Remote Similarity	NPD7236	Approved
0.622	Remote Similarity	NPD4767	Approved
0.622	Remote Similarity	NPD4768	Approved
0.6218	Remote Similarity	NPD5207	Approved
0.6198	Remote Similarity	NPD6001	Approved
0.6195	Remote Similarity	NPD7514	Phase 3
0.6195	Remote Similarity	NPD6930	Phase 2
0.6195	Remote Similarity	NPD6931	Approved
0.619	Remote Similarity	NPD4754	Approved
0.6186	Remote Similarity	NPD5737	Approved
0.6186	Remote Similarity	NPD6672	Approved
0.6167	Remote Similarity	NPD6050	Approved
0.6167	Remote Similarity	NPD5693	Phase 1
0.6167	Remote Similarity	NPD5694	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