NPASS Compound

Structure

NPC224532 OpenBabel07101718192D 22 23 0 0 1 0 0 0 0 0999 V2000 -2.7884 2.8335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1051 2.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4810 -0.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1093 -2.8133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1140 0.9935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6062 -2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2962 -1.3663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6343 -2.3258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1538 -1.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5082 -0.8612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1138 0.5440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4344 0.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0646 2.1434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4855 -0.3844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6893 -1.9987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0712 -1.2127 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3004 1.1716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9761 -0.2172 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2992 1.1240 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 -3.6263 2.0690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8034 0.5955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 15 16 1 0 0 0 0 16 9 1 1 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 6 0 0 0 19 21 1 6 0 0 0 20 5 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	347.034
LogP:	3.846
LogD:	3.713
LogS:	-4.164
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.705
Synthetic Accessibility Score:	5.073
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.541
MDCK Permeability:	2.5268713216064498e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.714
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.871
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.829
Plasma Protein Binding (PPB):	83.36195373535156%
Volume Distribution (VD):	0.719
Pgp-substrate:	13.237604141235352%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.272
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.333
CYP3A4-inhibitor:	0.605
CYP3A4-substrate:	0.388

ADMET: Excretion

Clearance (CL):	9.642
Half-life (T1/2):	0.299

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.455
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.037
Carcinogencity:	0.431
Eye Corrosion:	0.004
Eye Irritation:	0.07
Respiratory Toxicity:	0.581

Download Data

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

Natural Product: NPC224532

Natural Product ID:	NPC224532
*Common Name:**	Sarcophytol L
IUPAC Name:	(3S,3aS,4Z,6S,8E,12aR)-3,8-dimethyl-12-methylidene-5-propan-2-yl-1,2,3a,6,7,10,11,12a-octahydrocyclopenta[11]annulene-3,6-diol
Synonyms:	Sarcophytol L
Standard InCHIKey:	YMOPJGVZPYEQEV-WZQDFRNESA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-13(2)17-12-18-16(9-10-20(18,5)22)15(4)8-6-7-14(3)11-19(17)21/h7,12-13,16,18-19,21-22H,4,6,8-11H2,1-3,5H3/b14-7+,17-12-/t16-,18-,19-,20-/m0/s1
SMILES:	C/C/1=CCCC(=C)[C@H]2[C@H](/C=C([C@H](C1)O)/C(C)C)[C@@](CC2)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520720
PubChem CID:	11609191
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921403]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16124762]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16989519]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17917291]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[18198839]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561904]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	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
ED50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	12.6	ug ml-1	PMID[480731]

☑ 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 NPC224532 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	146
0.1-0.2	1545
0.2-0.3	10365
0.3-0.4	15110
0.4-0.5	7956
0.5-0.6	5598
0.6-0.7	1676
0.7-0.8	271
0.8-0.85	23
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.8732	High Similarity	NPC310643
0.873	High Similarity	NPC122239
0.8714	High Similarity	NPC471659
0.8636	High Similarity	NPC238352
0.8636	High Similarity	NPC477009
0.8615	High Similarity	NPC474480
0.8485	Intermediate Similarity	NPC309300
0.8438	Intermediate Similarity	NPC475931
0.8429	Intermediate Similarity	NPC471662
0.8382	Intermediate Similarity	NPC472255
0.8382	Intermediate Similarity	NPC477791
0.8382	Intermediate Similarity	NPC472253
0.8382	Intermediate Similarity	NPC136813
0.8358	Intermediate Similarity	NPC19569
0.8333	Intermediate Similarity	NPC279200
0.831	Intermediate Similarity	NPC234527
0.831	Intermediate Similarity	NPC14352
0.8308	Intermediate Similarity	NPC252809
0.8289	Intermediate Similarity	NPC472465
0.8281	Intermediate Similarity	NPC226848
0.8261	Intermediate Similarity	NPC167527
0.8235	Intermediate Similarity	NPC272125
0.8219	Intermediate Similarity	NPC126969
0.8219	Intermediate Similarity	NPC471658
0.8194	Intermediate Similarity	NPC309178
0.8182	Intermediate Similarity	NPC210346
0.8182	Intermediate Similarity	NPC274704
0.8169	Intermediate Similarity	NPC471660
0.8154	Intermediate Similarity	NPC469321
0.8088	Intermediate Similarity	NPC308844
0.8082	Intermediate Similarity	NPC313185
0.806	Intermediate Similarity	NPC473508
0.803	Intermediate Similarity	NPC99487
0.803	Intermediate Similarity	NPC471081
0.8028	Intermediate Similarity	NPC471781
0.8028	Intermediate Similarity	NPC470041
0.8	Intermediate Similarity	NPC181872
0.8	Intermediate Similarity	NPC155025
0.8	Intermediate Similarity	NPC305698
0.7971	Intermediate Similarity	NPC267027
0.7945	Intermediate Similarity	NPC329090
0.7945	Intermediate Similarity	NPC27395
0.7941	Intermediate Similarity	NPC300593
0.7922	Intermediate Similarity	NPC264245
0.7922	Intermediate Similarity	NPC471661
0.7917	Intermediate Similarity	NPC41886
0.791	Intermediate Similarity	NPC63111
0.7895	Intermediate Similarity	NPC81306
0.7895	Intermediate Similarity	NPC28862
0.7895	Intermediate Similarity	NPC47982
0.7895	Intermediate Similarity	NPC109546
0.7895	Intermediate Similarity	NPC84694
0.7895	Intermediate Similarity	NPC143182
0.7887	Intermediate Similarity	NPC90115
0.7887	Intermediate Similarity	NPC217570
0.7887	Intermediate Similarity	NPC144647
0.7879	Intermediate Similarity	NPC5698
0.7875	Intermediate Similarity	NPC293287
0.7875	Intermediate Similarity	NPC152808
0.7867	Intermediate Similarity	NPC476439
0.7857	Intermediate Similarity	NPC259299
0.7857	Intermediate Similarity	NPC73603
0.7857	Intermediate Similarity	NPC114651
0.7838	Intermediate Similarity	NPC319090
0.7838	Intermediate Similarity	NPC328104
0.7838	Intermediate Similarity	NPC23231
0.7838	Intermediate Similarity	NPC60818
0.7826	Intermediate Similarity	NPC469326
0.7826	Intermediate Similarity	NPC261782
0.7826	Intermediate Similarity	NPC205618
0.7821	Intermediate Similarity	NPC49964
0.7792	Intermediate Similarity	NPC164840
0.7792	Intermediate Similarity	NPC209944
0.7792	Intermediate Similarity	NPC234193
0.7792	Intermediate Similarity	NPC324772
0.7792	Intermediate Similarity	NPC241290
0.7778	Intermediate Similarity	NPC254845
0.7763	Intermediate Similarity	NPC477522
0.7763	Intermediate Similarity	NPC474216
0.7763	Intermediate Similarity	NPC39547
0.7763	Intermediate Similarity	NPC477514
0.7763	Intermediate Similarity	NPC470944
0.7763	Intermediate Similarity	NPC27949
0.7763	Intermediate Similarity	NPC323249
0.7763	Intermediate Similarity	NPC260814
0.7761	Intermediate Similarity	NPC323153
0.7761	Intermediate Similarity	NPC240506
0.7761	Intermediate Similarity	NPC66020
0.7733	Intermediate Similarity	NPC247325
0.7733	Intermediate Similarity	NPC315261
0.7733	Intermediate Similarity	NPC244488
0.7722	Intermediate Similarity	NPC472473
0.7722	Intermediate Similarity	NPC474634
0.7722	Intermediate Similarity	NPC475789
0.7722	Intermediate Similarity	NPC477667
0.7714	Intermediate Similarity	NPC311736
0.7714	Intermediate Similarity	NPC326310
0.7714	Intermediate Similarity	NPC162309
0.7692	Intermediate Similarity	NPC23852
0.7692	Intermediate Similarity	NPC47761
0.7692	Intermediate Similarity	NPC88735
0.7692	Intermediate Similarity	NPC472471
0.7692	Intermediate Similarity	NPC209620
0.7692	Intermediate Similarity	NPC320525
0.7662	Intermediate Similarity	NPC209430
0.7662	Intermediate Similarity	NPC30986
0.7647	Intermediate Similarity	NPC207007
0.7647	Intermediate Similarity	NPC321867
0.7647	Intermediate Similarity	NPC68679
0.7639	Intermediate Similarity	NPC304690
0.7639	Intermediate Similarity	NPC269877
0.7639	Intermediate Similarity	NPC74722
0.7639	Intermediate Similarity	NPC329989
0.7639	Intermediate Similarity	NPC239373
0.7639	Intermediate Similarity	NPC167272
0.7632	Intermediate Similarity	NPC318495
0.7632	Intermediate Similarity	NPC155986
0.7632	Intermediate Similarity	NPC198968
0.7625	Intermediate Similarity	NPC205845
0.7625	Intermediate Similarity	NPC238485
0.7606	Intermediate Similarity	NPC163290
0.76	Intermediate Similarity	NPC113639
0.7595	Intermediate Similarity	NPC87489
0.7595	Intermediate Similarity	NPC189972
0.7595	Intermediate Similarity	NPC7414
0.7595	Intermediate Similarity	NPC101462
0.7595	Intermediate Similarity	NPC218616
0.7595	Intermediate Similarity	NPC296701
0.7595	Intermediate Similarity	NPC50964
0.7576	Intermediate Similarity	NPC278550
0.7571	Intermediate Similarity	NPC187619
0.7568	Intermediate Similarity	NPC329763
0.7568	Intermediate Similarity	NPC474140
0.7564	Intermediate Similarity	NPC26117
0.7538	Intermediate Similarity	NPC329686
0.7536	Intermediate Similarity	NPC473759
0.7536	Intermediate Similarity	NPC474155
0.7534	Intermediate Similarity	NPC9161
0.7534	Intermediate Similarity	NPC133873
0.7534	Intermediate Similarity	NPC49422
0.7534	Intermediate Similarity	NPC34834
0.7534	Intermediate Similarity	NPC4299
0.7532	Intermediate Similarity	NPC473943
0.7531	Intermediate Similarity	NPC318390
0.7531	Intermediate Similarity	NPC274448
0.75	Intermediate Similarity	NPC474496
0.75	Intermediate Similarity	NPC107059
0.75	Intermediate Similarity	NPC472466
0.75	Intermediate Similarity	NPC96319
0.75	Intermediate Similarity	NPC320548
0.75	Intermediate Similarity	NPC470384
0.75	Intermediate Similarity	NPC321381
0.75	Intermediate Similarity	NPC321016
0.75	Intermediate Similarity	NPC317458
0.75	Intermediate Similarity	NPC279537
0.747	Intermediate Similarity	NPC471952
0.7468	Intermediate Similarity	NPC474731
0.7468	Intermediate Similarity	NPC7505
0.7468	Intermediate Similarity	NPC474683
0.7468	Intermediate Similarity	NPC474752
0.7468	Intermediate Similarity	NPC316844
0.7468	Intermediate Similarity	NPC474759
0.7468	Intermediate Similarity	NPC47031
0.7468	Intermediate Similarity	NPC82986
0.7465	Intermediate Similarity	NPC202017
0.7463	Intermediate Similarity	NPC475830
0.746	Intermediate Similarity	NPC473672
0.746	Intermediate Similarity	NPC474495
0.7439	Intermediate Similarity	NPC477668
0.7439	Intermediate Similarity	NPC6391
0.7439	Intermediate Similarity	NPC261266
0.7436	Intermediate Similarity	NPC328714
0.7436	Intermediate Similarity	NPC1319
0.7436	Intermediate Similarity	NPC201225
0.7432	Intermediate Similarity	NPC472254
0.7429	Intermediate Similarity	NPC290367
0.7429	Intermediate Similarity	NPC140233
0.7429	Intermediate Similarity	NPC110241
0.7429	Intermediate Similarity	NPC287744
0.7412	Intermediate Similarity	NPC472468
0.7407	Intermediate Similarity	NPC231310
0.7407	Intermediate Similarity	NPC474047
0.7407	Intermediate Similarity	NPC185568
0.7403	Intermediate Similarity	NPC474826
0.7403	Intermediate Similarity	NPC276769
0.7403	Intermediate Similarity	NPC477426
0.7403	Intermediate Similarity	NPC476703
0.7403	Intermediate Similarity	NPC477425
0.7403	Intermediate Similarity	NPC477427
0.7397	Intermediate Similarity	NPC473893
0.7397	Intermediate Similarity	NPC22301
0.7397	Intermediate Similarity	NPC101622
0.7397	Intermediate Similarity	NPC471560
0.7391	Intermediate Similarity	NPC475251
0.7391	Intermediate Similarity	NPC225342
0.7381	Intermediate Similarity	NPC2983
0.7375	Intermediate Similarity	NPC470614
0.7375	Intermediate Similarity	NPC133844
0.7375	Intermediate Similarity	NPC1272
0.7375	Intermediate Similarity	NPC202389

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 NPC224532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	2161
0.2-0.3	4385
0.3-0.4	1745
0.4-0.5	420
0.5-0.6	206
0.6-0.7	55
0.7-0.8	37
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
0.8026	Intermediate Similarity	NPD4819	Approved
0.8026	Intermediate Similarity	NPD4820	Approved
0.8026	Intermediate Similarity	NPD4821	Approved
0.8026	Intermediate Similarity	NPD4822	Approved
0.7949	Intermediate Similarity	NPD5331	Approved
0.7949	Intermediate Similarity	NPD5362	Discontinued
0.7949	Intermediate Similarity	NPD5332	Approved
0.7945	Intermediate Similarity	NPD6926	Approved
0.7945	Intermediate Similarity	NPD6924	Approved
0.7922	Intermediate Similarity	NPD4790	Discontinued
0.7792	Intermediate Similarity	NPD6931	Approved
0.7792	Intermediate Similarity	NPD6930	Phase 2
0.7792	Intermediate Similarity	NPD7514	Phase 3
0.7763	Intermediate Similarity	NPD4271	Approved
0.7763	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD4268	Approved
0.7733	Intermediate Similarity	NPD6933	Approved
0.7662	Intermediate Similarity	NPD6929	Approved
0.7647	Intermediate Similarity	NPD368	Approved
0.7639	Intermediate Similarity	NPD6923	Approved
0.7639	Intermediate Similarity	NPD6922	Approved
0.7632	Intermediate Similarity	NPD5776	Phase 2
0.7632	Intermediate Similarity	NPD6925	Approved
0.7595	Intermediate Similarity	NPD4270	Approved
0.7595	Intermediate Similarity	NPD4269	Approved
0.7564	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7332	Phase 2
0.7561	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD7144	Approved
0.7534	Intermediate Similarity	NPD7143	Approved
0.7532	Intermediate Similarity	NPD7145	Approved
0.75	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6695	Phase 3
0.7468	Intermediate Similarity	NPD6902	Approved
0.7432	Intermediate Similarity	NPD7151	Approved
0.7432	Intermediate Similarity	NPD7152	Approved
0.7432	Intermediate Similarity	NPD7150	Approved
0.7407	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6932	Approved
0.7368	Intermediate Similarity	NPD7339	Approved
0.7368	Intermediate Similarity	NPD6942	Approved
0.7342	Intermediate Similarity	NPD4252	Approved
0.7317	Intermediate Similarity	NPD5363	Approved
0.7317	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6893	Approved
0.7308	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6898	Phase 1
0.725	Intermediate Similarity	NPD5369	Approved
0.7237	Intermediate Similarity	NPD4784	Approved
0.7237	Intermediate Similarity	NPD4785	Approved
0.7229	Intermediate Similarity	NPD5786	Approved
0.7215	Intermediate Similarity	NPD6683	Phase 2
0.72	Intermediate Similarity	NPD4243	Approved
0.7143	Intermediate Similarity	NPD7524	Approved
0.7143	Intermediate Similarity	NPD8264	Approved
0.7143	Intermediate Similarity	NPD7750	Discontinued
0.7125	Intermediate Similarity	NPD7509	Discontinued
0.7125	Intermediate Similarity	NPD7525	Registered
0.7073	Intermediate Similarity	NPD7154	Phase 3
0.7015	Intermediate Similarity	NPD342	Phase 1
0.6941	Remote Similarity	NPD4251	Approved
0.6941	Remote Similarity	NPD4250	Approved
0.6914	Remote Similarity	NPD4748	Discontinued
0.6914	Remote Similarity	NPD5368	Approved
0.6897	Remote Similarity	NPD5785	Approved
0.6824	Remote Similarity	NPD4249	Approved
0.6818	Remote Similarity	NPD7087	Discontinued
0.6786	Remote Similarity	NPD4786	Approved
0.6747	Remote Similarity	NPD6435	Approved
0.6709	Remote Similarity	NPD5275	Approved
0.6709	Remote Similarity	NPD4190	Phase 3
0.6667	Remote Similarity	NPD4265	Approved
0.6629	Remote Similarity	NPD7637	Suspended
0.6588	Remote Similarity	NPD3133	Approved
0.6588	Remote Similarity	NPD3666	Approved
0.6588	Remote Similarity	NPD3665	Phase 1
0.6585	Remote Similarity	NPD4195	Approved
0.6548	Remote Similarity	NPD3667	Approved
0.6456	Remote Similarity	NPD4732	Discontinued
0.6404	Remote Similarity	NPD6051	Approved
0.6404	Remote Similarity	NPD4753	Phase 2
0.6374	Remote Similarity	NPD4202	Approved
0.6353	Remote Similarity	NPD4221	Approved
0.6353	Remote Similarity	NPD4223	Phase 3
0.6344	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7136	Phase 2
0.6322	Remote Similarity	NPD5329	Approved
0.6279	Remote Similarity	NPD4788	Approved
0.625	Remote Similarity	NPD5279	Phase 3
0.6222	Remote Similarity	NPD5328	Approved
0.6222	Remote Similarity	NPD5370	Suspended
0.6207	Remote Similarity	NPD4197	Approved
0.6207	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD4219	Approved
0.619	Remote Similarity	NPD7645	Phase 2
0.6186	Remote Similarity	NPD5211	Phase 2
0.6184	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD3198	Approved
0.6146	Remote Similarity	NPD7639	Approved
0.6146	Remote Similarity	NPD7640	Approved
0.6111	Remote Similarity	NPD4518	Approved
0.6105	Remote Similarity	NPD4755	Approved
0.6105	Remote Similarity	NPD6083	Phase 2
0.6105	Remote Similarity	NPD6084	Phase 2
0.6104	Remote Similarity	NPD7331	Phase 2
0.6087	Remote Similarity	NPD6079	Approved
0.6087	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5690	Phase 2
0.6067	Remote Similarity	NPD4690	Approved
0.6067	Remote Similarity	NPD4689	Approved
0.6067	Remote Similarity	NPD5205	Approved
0.6067	Remote Similarity	NPD4688	Approved
0.6067	Remote Similarity	NPD4694	Approved
0.6067	Remote Similarity	NPD3618	Phase 1
0.6067	Remote Similarity	NPD4693	Phase 3
0.6067	Remote Similarity	NPD4138	Approved
0.6067	Remote Similarity	NPD5280	Approved
0.6064	Remote Similarity	NPD5210	Approved
0.6064	Remote Similarity	NPD4629	Approved
0.6061	Remote Similarity	NPD5141	Approved
0.6042	Remote Similarity	NPD7638	Approved
0.6023	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5779	Approved
0.6022	Remote Similarity	NPD6399	Phase 3
0.6022	Remote Similarity	NPD5778	Approved
0.5979	Remote Similarity	NPD4700	Approved
0.5979	Remote Similarity	NPD4696	Approved
0.5979	Remote Similarity	NPD5286	Approved
0.5979	Remote Similarity	NPD5285	Approved
0.5978	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6053	Discontinued
0.596	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD1696	Phase 3
0.5934	Remote Similarity	NPD4722	Approved
0.5934	Remote Similarity	NPD4723	Approved
0.5922	Remote Similarity	NPD6371	Approved
0.5918	Remote Similarity	NPD5223	Approved
0.5914	Remote Similarity	NPD7983	Approved
0.5895	Remote Similarity	NPD5695	Phase 3
0.5889	Remote Similarity	NPD7521	Approved
0.5889	Remote Similarity	NPD6409	Approved
0.5889	Remote Similarity	NPD5330	Approved
0.5889	Remote Similarity	NPD7334	Approved
0.5889	Remote Similarity	NPD6684	Approved
0.5889	Remote Similarity	NPD7146	Approved
0.5882	Remote Similarity	NPD6406	Approved
0.5862	Remote Similarity	NPD4692	Approved
0.5862	Remote Similarity	NPD4139	Approved
0.5859	Remote Similarity	NPD5226	Approved
0.5859	Remote Similarity	NPD5224	Approved
0.5859	Remote Similarity	NPD4633	Approved
0.5859	Remote Similarity	NPD5225	Approved
0.5843	Remote Similarity	NPD3668	Phase 3
0.5842	Remote Similarity	NPD6640	Phase 3
0.5842	Remote Similarity	NPD6402	Approved
0.5842	Remote Similarity	NPD7128	Approved
0.5842	Remote Similarity	NPD6675	Approved
0.5842	Remote Similarity	NPD5739	Approved
0.5806	Remote Similarity	NPD46	Approved
0.5806	Remote Similarity	NPD7838	Discovery
0.5806	Remote Similarity	NPD6698	Approved
0.5806	Remote Similarity	NPD4096	Approved
0.5802	Remote Similarity	NPD4787	Phase 1
0.58	Remote Similarity	NPD5175	Approved
0.58	Remote Similarity	NPD5174	Approved
0.58	Remote Similarity	NPD4754	Approved
0.5784	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7341	Phase 2
0.5769	Remote Similarity	NPD6420	Discontinued
0.5761	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD6903	Approved
0.5758	Remote Similarity	NPD5344	Discontinued
0.5758	Remote Similarity	NPD4159	Approved
0.5745	Remote Similarity	NPD5284	Approved
0.5745	Remote Similarity	NPD5281	Approved
0.573	Remote Similarity	NPD6110	Phase 1
0.5728	Remote Similarity	NPD6899	Approved
0.5728	Remote Similarity	NPD6881	Approved
0.5728	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4225	Approved
0.5714	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD4519	Discontinued
0.5714	Remote Similarity	NPD6098	Approved
0.5714	Remote Similarity	NPD4623	Approved
0.5699	Remote Similarity	NPD6101	Approved
0.5699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD1695	Approved
0.5686	Remote Similarity	NPD7333	Discontinued
0.5686	Remote Similarity	NPD4768	Approved
0.5686	Remote Similarity	NPD4767	Approved
0.5673	Remote Similarity	NPD6372	Approved
0.5673	Remote Similarity	NPD6373	Approved
0.567	Remote Similarity	NPD7839	Suspended
0.567	Remote Similarity	NPD5221	Approved
0.567	Remote Similarity	NPD4697	Phase 3
0.567	Remote Similarity	NPD5222	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