NPASS Compound

Structure

CID106872 OpenBabel06191715452D 22 21 0 0 1 0 0 0 0 0999 V2000 7.7942 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 12 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.22
Volume:	613.023
LogP:	3.345
LogD:	1.376
LogS:	-3.788
# Rotatable Bonds:	11
TPSA:	171.96
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.34
Synthetic Accessibility Score:	5.866
Fsp3:	0.485
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.436
MDCK Permeability:	5.403676914284006e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.081
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.612
Plasma Protein Binding (PPB):	78.65181732177734%
Volume Distribution (VD):	1.194
Pgp-substrate:	21.499427795410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.305
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.138
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.425

ADMET: Excretion

Clearance (CL):	5.772
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.256
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.284
Carcinogencity:	0.422
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.677

Download Data

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

Natural Product: NPC106872

Natural Product ID:	NPC106872
*Common Name:**	Methyl 12-Hydroxyoctadecanoate
IUPAC Name:	methyl 12-hydroxyoctadecanoate
Synonyms:
Standard InCHIKey:	RVWOWEQKPMPWMQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H38O3/c1-3-4-5-12-15-18(20)16-13-10-8-6-7-9-11-14-17-19(21)22-2/h18,20H,3-17H2,1-2H3
SMILES:	CCCCCCC(CCCCCCCCCCC(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2139695
PubChem CID:	8840
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO25547	Spirodela polyrhiza	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
Potency	7

Activity Type	# Activity
Individual Protein	1
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Potency	n.a.	4364.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	9688.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19496.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24544.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54947.7	nM	PubChem BioAssay data set
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[488942]

☑ 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 NPC106872 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	724
0.1-0.2	8093
0.2-0.3	17394
0.3-0.4	9711
0.4-0.5	5366
0.5-0.6	1043
0.6-0.7	250
0.7-0.8	58
0.8-0.85	32
0.85-0.9	19
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC324004
0.9773	High Similarity	NPC328497
0.9545	High Similarity	NPC12438
0.9545	High Similarity	NPC30195
0.9149	High Similarity	NPC90904
0.8936	High Similarity	NPC304162
0.8889	High Similarity	NPC287231
0.8889	High Similarity	NPC469781
0.8889	High Similarity	NPC47363
0.88	High Similarity	NPC320588
0.88	High Similarity	NPC469937
0.88	High Similarity	NPC23155
0.88	High Similarity	NPC53463
0.8723	High Similarity	NPC131770
0.8723	High Similarity	NPC200618
0.8667	High Similarity	NPC74845
0.8636	High Similarity	NPC171736
0.8636	High Similarity	NPC307783
0.8636	High Similarity	NPC216630
0.8636	High Similarity	NPC196924
0.8636	High Similarity	NPC149184
0.8636	High Similarity	NPC209970
0.8542	High Similarity	NPC26253
0.8444	Intermediate Similarity	NPC203531
0.8444	Intermediate Similarity	NPC236579
0.8444	Intermediate Similarity	NPC67462
0.8409	Intermediate Similarity	NPC161097
0.8409	Intermediate Similarity	NPC28598
0.82	Intermediate Similarity	NPC100096
0.8182	Intermediate Similarity	NPC14227
0.8182	Intermediate Similarity	NPC154186
0.8182	Intermediate Similarity	NPC301696
0.8182	Intermediate Similarity	NPC201844
0.8182	Intermediate Similarity	NPC279026
0.8182	Intermediate Similarity	NPC261080
0.8182	Intermediate Similarity	NPC301585
0.8182	Intermediate Similarity	NPC113928
0.8085	Intermediate Similarity	NPC8219
0.8	Intermediate Similarity	NPC165533
0.8	Intermediate Similarity	NPC149299
0.8	Intermediate Similarity	NPC55678
0.8	Intermediate Similarity	NPC40597
0.8	Intermediate Similarity	NPC250028
0.8	Intermediate Similarity	NPC12156
0.8	Intermediate Similarity	NPC256163
0.8	Intermediate Similarity	NPC470363
0.7955	Intermediate Similarity	NPC201622
0.7955	Intermediate Similarity	NPC22903
0.7955	Intermediate Similarity	NPC54980
0.7955	Intermediate Similarity	NPC305660
0.7917	Intermediate Similarity	NPC145045
0.7917	Intermediate Similarity	NPC52700
0.7917	Intermediate Similarity	NPC105329
0.7917	Intermediate Similarity	NPC63182
0.7872	Intermediate Similarity	NPC76051
0.7872	Intermediate Similarity	NPC317128
0.7872	Intermediate Similarity	NPC19305
0.7872	Intermediate Similarity	NPC255837
0.7843	Intermediate Similarity	NPC287811
0.7826	Intermediate Similarity	NPC53541
0.7778	Intermediate Similarity	NPC183424
0.7778	Intermediate Similarity	NPC294085
0.7778	Intermediate Similarity	NPC31551
0.7778	Intermediate Similarity	NPC214610
0.7778	Intermediate Similarity	NPC80234
0.7778	Intermediate Similarity	NPC219536
0.7778	Intermediate Similarity	NPC118968
0.7778	Intermediate Similarity	NPC223249
0.7755	Intermediate Similarity	NPC326957
0.7755	Intermediate Similarity	NPC21844
0.7719	Intermediate Similarity	NPC201939
0.7708	Intermediate Similarity	NPC273545
0.766	Intermediate Similarity	NPC129972
0.766	Intermediate Similarity	NPC71317
0.766	Intermediate Similarity	NPC301528
0.76	Intermediate Similarity	NPC477878
0.76	Intermediate Similarity	NPC324793
0.7556	Intermediate Similarity	NPC268826
0.7544	Intermediate Similarity	NPC243532
0.75	Intermediate Similarity	NPC155263
0.75	Intermediate Similarity	NPC474914
0.75	Intermediate Similarity	NPC474392
0.7458	Intermediate Similarity	NPC314103
0.7447	Intermediate Similarity	NPC103286
0.7447	Intermediate Similarity	NPC163746
0.7368	Intermediate Similarity	NPC17935
0.7347	Intermediate Similarity	NPC55023
0.7333	Intermediate Similarity	NPC128996
0.7333	Intermediate Similarity	NPC476330
0.7292	Intermediate Similarity	NPC176500
0.7288	Intermediate Similarity	NPC235788
0.7273	Intermediate Similarity	NPC156630
0.7273	Intermediate Similarity	NPC97967
0.7273	Intermediate Similarity	NPC317203
0.72	Intermediate Similarity	NPC314679
0.717	Intermediate Similarity	NPC314084
0.7167	Intermediate Similarity	NPC68343
0.7167	Intermediate Similarity	NPC328089
0.7111	Intermediate Similarity	NPC154642
0.7111	Intermediate Similarity	NPC134782
0.7111	Intermediate Similarity	NPC80396
0.7111	Intermediate Similarity	NPC80641
0.7097	Intermediate Similarity	NPC469925
0.7097	Intermediate Similarity	NPC330426
0.7097	Intermediate Similarity	NPC271921
0.7097	Intermediate Similarity	NPC148192
0.7097	Intermediate Similarity	NPC22101
0.7097	Intermediate Similarity	NPC104537
0.7097	Intermediate Similarity	NPC127091
0.7097	Intermediate Similarity	NPC206601
0.7091	Intermediate Similarity	NPC289979
0.7059	Intermediate Similarity	NPC249754
0.7049	Intermediate Similarity	NPC255863
0.7049	Intermediate Similarity	NPC136164
0.7049	Intermediate Similarity	NPC245947
0.7037	Intermediate Similarity	NPC310746
0.7	Intermediate Similarity	NPC474552
0.6984	Remote Similarity	NPC141481
0.6984	Remote Similarity	NPC48218
0.6984	Remote Similarity	NPC473559
0.6984	Remote Similarity	NPC324981
0.6984	Remote Similarity	NPC82315
0.6957	Remote Similarity	NPC74352
0.6939	Remote Similarity	NPC289686
0.6909	Remote Similarity	NPC72722
0.6889	Remote Similarity	NPC301398
0.6889	Remote Similarity	NPC223374
0.6889	Remote Similarity	NPC196442
0.6889	Remote Similarity	NPC86545
0.6885	Remote Similarity	NPC470320
0.6885	Remote Similarity	NPC226592
0.6875	Remote Similarity	NPC285003
0.6875	Remote Similarity	NPC241265
0.6863	Remote Similarity	NPC308301
0.6852	Remote Similarity	NPC470412
0.6852	Remote Similarity	NPC470410
0.6852	Remote Similarity	NPC470411
0.6842	Remote Similarity	NPC477201
0.6833	Remote Similarity	NPC321838
0.6833	Remote Similarity	NPC328776
0.6833	Remote Similarity	NPC469923
0.6833	Remote Similarity	NPC320305
0.6825	Remote Similarity	NPC26500
0.6825	Remote Similarity	NPC286842
0.6825	Remote Similarity	NPC473829
0.6825	Remote Similarity	NPC99619
0.6825	Remote Similarity	NPC475443
0.6818	Remote Similarity	NPC139131
0.6818	Remote Similarity	NPC175342
0.6818	Remote Similarity	NPC152759
0.6818	Remote Similarity	NPC185538
0.6818	Remote Similarity	NPC193062
0.6818	Remote Similarity	NPC66124
0.6818	Remote Similarity	NPC181516
0.6818	Remote Similarity	NPC1748
0.6818	Remote Similarity	NPC12231
0.6818	Remote Similarity	NPC291158
0.6818	Remote Similarity	NPC319034
0.6818	Remote Similarity	NPC205141
0.6818	Remote Similarity	NPC72324
0.6818	Remote Similarity	NPC272998
0.6809	Remote Similarity	NPC73245
0.6786	Remote Similarity	NPC154245
0.6786	Remote Similarity	NPC424
0.6786	Remote Similarity	NPC261831
0.6786	Remote Similarity	NPC25417
0.6786	Remote Similarity	NPC6095
0.6786	Remote Similarity	NPC88966
0.6786	Remote Similarity	NPC281972
0.6786	Remote Similarity	NPC87394
0.6786	Remote Similarity	NPC85813
0.6786	Remote Similarity	NPC32467
0.6786	Remote Similarity	NPC290563
0.6786	Remote Similarity	NPC87564
0.678	Remote Similarity	NPC475821
0.678	Remote Similarity	NPC472019
0.678	Remote Similarity	NPC472020
0.678	Remote Similarity	NPC226602
0.678	Remote Similarity	NPC469924
0.6774	Remote Similarity	NPC326268
0.6774	Remote Similarity	NPC318420
0.6769	Remote Similarity	NPC476660
0.6769	Remote Similarity	NPC321873
0.6769	Remote Similarity	NPC470268
0.6769	Remote Similarity	NPC42526
0.6735	Remote Similarity	NPC325452
0.6735	Remote Similarity	NPC248763
0.6721	Remote Similarity	NPC325773
0.6719	Remote Similarity	NPC97736
0.6719	Remote Similarity	NPC50228
0.6719	Remote Similarity	NPC319007
0.6667	Remote Similarity	NPC305182
0.6667	Remote Similarity	NPC28779
0.6667	Remote Similarity	NPC10316
0.6667	Remote Similarity	NPC52264
0.6667	Remote Similarity	NPC94368
0.6667	Remote Similarity	NPC286498
0.6667	Remote Similarity	NPC223677
0.6667	Remote Similarity	NPC81263
0.6667	Remote Similarity	NPC200845

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 NPC106872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1108
0.1-0.2	4675
0.2-0.3	2116
0.3-0.4	828
0.4-0.5	277
0.5-0.6	108
0.6-0.7	25
0.7-0.8	6
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD2699	Approved
0.88	High Similarity	NPD3730	Approved
0.88	High Similarity	NPD3728	Approved
0.8636	High Similarity	NPD2270	Approved
0.8431	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD9448	Phase 2
0.8182	Intermediate Similarity	NPD633	Phase 3
0.8085	Intermediate Similarity	NPD3199	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6125	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD3206	Approved
0.7778	Intermediate Similarity	NPD9655	Approved
0.7679	Intermediate Similarity	NPD3198	Approved
0.72	Intermediate Similarity	NPD634	Phase 3
0.7167	Intermediate Similarity	NPD7909	Approved
0.7167	Intermediate Similarity	NPD3197	Phase 1
0.7037	Intermediate Similarity	NPD3186	Phase 1
0.6923	Remote Similarity	NPD2266	Phase 2
0.6818	Remote Similarity	NPD2272	Approved
0.6818	Remote Similarity	NPD5383	Approved
0.6786	Remote Similarity	NPD4266	Approved
0.6786	Remote Similarity	NPD3196	Approved
0.6786	Remote Similarity	NPD3194	Approved
0.6786	Remote Similarity	NPD3195	Phase 2
0.6607	Remote Similarity	NPD3172	Approved
0.6604	Remote Similarity	NPD622	Approved
0.66	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD9431	Approved
0.6538	Remote Similarity	NPD9430	Approved
0.6491	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD9450	Approved
0.6327	Remote Similarity	NPD77	Approved
0.6271	Remote Similarity	NPD73	Approved
0.625	Remote Similarity	NPD28	Approved
0.625	Remote Similarity	NPD29	Approved
0.6232	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7536	Approved
0.6122	Remote Similarity	NPD9513	Phase 1
0.6119	Remote Similarity	NPD8277	Approved
0.6056	Remote Similarity	NPD6117	Approved
0.5972	Remote Similarity	NPD6116	Phase 1
0.597	Remote Similarity	NPD8278	Approved
0.5965	Remote Similarity	NPD9638	Phase 2
0.5957	Remote Similarity	NPD8857	Approved
0.5942	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD3704	Approved
0.5893	Remote Similarity	NPD3173	Approved
0.589	Remote Similarity	NPD6118	Approved
0.589	Remote Similarity	NPD4802	Phase 2
0.589	Remote Similarity	NPD4238	Approved
0.589	Remote Similarity	NPD6697	Approved
0.589	Remote Similarity	NPD6115	Approved
0.589	Remote Similarity	NPD6114	Approved
0.5867	Remote Similarity	NPD5369	Approved
0.5862	Remote Similarity	NPD66	Approved
0.5862	Remote Similarity	NPD9009	Approved
0.5862	Remote Similarity	NPD9008	Approved
0.5862	Remote Similarity	NPD9007	Approved
0.5862	Remote Similarity	NPD8960	Approved
0.5862	Remote Similarity	NPD64	Approved
0.5862	Remote Similarity	NPD72	Approved
0.5862	Remote Similarity	NPD9011	Approved
0.5862	Remote Similarity	NPD65	Approved
0.5862	Remote Similarity	NPD9010	Approved
0.5821	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD4244	Approved
0.5797	Remote Similarity	NPD4245	Approved
0.5789	Remote Similarity	NPD6435	Approved
0.5758	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD5368	Approved
0.5714	Remote Similarity	NPD5362	Discontinued
0.5714	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5777	Approved
0.5714	Remote Similarity	NPD7154	Phase 3
0.5714	Remote Similarity	NPD370	Phase 3
0.5694	Remote Similarity	NPD3702	Approved
0.5676	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD4224	Phase 2
0.5652	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD8618	Approved
0.5652	Remote Similarity	NPD3698	Phase 2
0.5645	Remote Similarity	NPD8959	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