NPASS Compound

Structure

NPC96663 OpenBabel07101718332D 24 23 0 0 1 0 0 0 0 0999 V2000 -7.7942 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 -7.7942 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 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 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 18 1 0 0 0 0 2 18 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 24 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.32
Volume:	401.376
LogP:	7.912
LogD:	6.568
LogS:	-6.828
# Rotatable Bonds:	15
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	3.298
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.712
MDCK Permeability:	1.4814181668043602e-05
Pgp-inhibitor:	0.781
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.396
Plasma Protein Binding (PPB):	99.06226348876953%
Volume Distribution (VD):	1.557
Pgp-substrate:	2.5468854904174805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.335
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.474
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.344
CYP2C9-substrate:	0.768
CYP2D6-inhibitor:	0.294
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.371
CYP3A4-substrate:	0.154

ADMET: Excretion

Clearance (CL):	4.047
Half-life (T1/2):	0.165

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.482
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.147
Skin Sensitization:	0.965
Carcinogencity:	0.03
Eye Corrosion:	0.894
Eye Irritation:	0.96
Respiratory Toxicity:	0.109

Download Data

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

Natural Product: NPC96663

Natural Product ID:	NPC96663
*Common Name:**	Trans-Phytyl Acetate
IUPAC Name:	[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl] acetate
Synonyms:
Standard InCHIKey:	JIGCTXHIECXYRJ-ILWBRPEASA-N
Standard InCHI:	InChI=1S/C22H42O2/c1-18(2)10-7-11-19(3)12-8-13-20(4)14-9-15-21(5)16-17-24-22(6)23/h16,18-20H,7-15,17H2,1-6H3/b21-16+/t19-,20-/m1/s1
SMILES:	C[C@@H](CCC/C(=C/COC(=O)C)/C)CCC[C@@H](CCCC(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3356397
PubChem CID:	637195
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001357] Acyclic 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
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23548547]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25497963]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	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	3
Others	5

Activity Type	# Activity
Cell Line	1
Individual Protein	6
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1210	Individual Protein	T-cell protein-tyrosine phosphatase	Homo sapiens	Inhibition	<	50.0	%	PMID[499348]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	50020.0	nM	PMID[499348]
NPT205	Individual Protein	Protein-tyrosine phosphatase 1C	Homo sapiens	Inhibition	<	50.0	%	PMID[499348]
NPT206	Individual Protein	Protein-tyrosine phosphatase 2C	Homo sapiens	Inhibition	<	50.0	%	PMID[499348]
NPT1870	Individual Protein	Receptor-type tyrosine-protein phosphatase F (LAR)	Homo sapiens	Inhibition	<	50.0	%	PMID[499348]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[499348]
NPT911	Individual Protein	Dual specificity phosphatase Cdc25B	Homo sapiens	Inhibition	<	50.0	%	PMID[499348]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[499348]

☑ 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 NPC96663 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	163
0.1-0.2	2614
0.2-0.3	14203
0.3-0.4	14596
0.4-0.5	6922
0.5-0.6	3424
0.6-0.7	674
0.7-0.8	91
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8814	High Similarity	NPC34883
0.8814	High Similarity	NPC329698
0.85	High Similarity	NPC226066
0.8387	Intermediate Similarity	NPC472266
0.8269	Intermediate Similarity	NPC197467
0.8125	Intermediate Similarity	NPC269841
0.8125	Intermediate Similarity	NPC101622
0.8077	Intermediate Similarity	NPC47946
0.8077	Intermediate Similarity	NPC26600
0.8	Intermediate Similarity	NPC4299
0.8	Intermediate Similarity	NPC19241
0.7937	Intermediate Similarity	NPC185587
0.7879	Intermediate Similarity	NPC477084
0.7879	Intermediate Similarity	NPC472254
0.7818	Intermediate Similarity	NPC289388
0.7742	Intermediate Similarity	NPC155849
0.7742	Intermediate Similarity	NPC217940
0.7727	Intermediate Similarity	NPC64234
0.7727	Intermediate Similarity	NPC37929
0.7727	Intermediate Similarity	NPC469660
0.7692	Intermediate Similarity	NPC276290
0.7679	Intermediate Similarity	NPC244452
0.7636	Intermediate Similarity	NPC135698
0.7612	Intermediate Similarity	NPC257618
0.7593	Intermediate Similarity	NPC128280
0.7586	Intermediate Similarity	NPC269615
0.7576	Intermediate Similarity	NPC232812
0.7544	Intermediate Similarity	NPC106531
0.7544	Intermediate Similarity	NPC170167
0.75	Intermediate Similarity	NPC471279
0.75	Intermediate Similarity	NPC477085
0.75	Intermediate Similarity	NPC26960
0.75	Intermediate Similarity	NPC476489
0.75	Intermediate Similarity	NPC476490
0.75	Intermediate Similarity	NPC222244
0.75	Intermediate Similarity	NPC16349
0.75	Intermediate Similarity	NPC471277
0.75	Intermediate Similarity	NPC142103
0.75	Intermediate Similarity	NPC135703
0.75	Intermediate Similarity	NPC182102
0.75	Intermediate Similarity	NPC236338
0.7463	Intermediate Similarity	NPC473361
0.7463	Intermediate Similarity	NPC329904
0.7429	Intermediate Similarity	NPC469880
0.7429	Intermediate Similarity	NPC301525
0.7419	Intermediate Similarity	NPC127824
0.7407	Intermediate Similarity	NPC270706
0.7391	Intermediate Similarity	NPC474758
0.7385	Intermediate Similarity	NPC191233
0.7368	Intermediate Similarity	NPC148056
0.7353	Intermediate Similarity	NPC477087
0.7353	Intermediate Similarity	NPC477086
0.7353	Intermediate Similarity	NPC181587
0.7324	Intermediate Similarity	NPC84360
0.7324	Intermediate Similarity	NPC476439
0.7321	Intermediate Similarity	NPC15912
0.7313	Intermediate Similarity	NPC265574
0.7313	Intermediate Similarity	NPC151481
0.7286	Intermediate Similarity	NPC228978
0.7273	Intermediate Similarity	NPC194871
0.7258	Intermediate Similarity	NPC143810
0.7258	Intermediate Similarity	NPC83838
0.7241	Intermediate Similarity	NPC151919
0.7231	Intermediate Similarity	NPC220766
0.7231	Intermediate Similarity	NPC470688
0.7222	Intermediate Similarity	NPC474005
0.7222	Intermediate Similarity	NPC12907
0.7213	Intermediate Similarity	NPC129150
0.7213	Intermediate Similarity	NPC294938
0.7213	Intermediate Similarity	NPC249850
0.7213	Intermediate Similarity	NPC293437
0.7193	Intermediate Similarity	NPC27264
0.7188	Intermediate Similarity	NPC44343
0.7188	Intermediate Similarity	NPC179087
0.7188	Intermediate Similarity	NPC210303
0.7183	Intermediate Similarity	NPC27205
0.7183	Intermediate Similarity	NPC4509
0.7183	Intermediate Similarity	NPC476317
0.717	Intermediate Similarity	NPC57923
0.7164	Intermediate Similarity	NPC470256
0.7143	Intermediate Similarity	NPC259599
0.7143	Intermediate Similarity	NPC299730
0.7143	Intermediate Similarity	NPC477204
0.7143	Intermediate Similarity	NPC117746
0.7143	Intermediate Similarity	NPC471278
0.7143	Intermediate Similarity	NPC140287
0.7143	Intermediate Similarity	NPC474551
0.7143	Intermediate Similarity	NPC15499
0.7143	Intermediate Similarity	NPC294434
0.7123	Intermediate Similarity	NPC477088
0.7123	Intermediate Similarity	NPC242767
0.7123	Intermediate Similarity	NPC471537
0.7123	Intermediate Similarity	NPC325869
0.7101	Intermediate Similarity	NPC129665
0.7101	Intermediate Similarity	NPC163003
0.7097	Intermediate Similarity	NPC254095
0.7097	Intermediate Similarity	NPC21946
0.7097	Intermediate Similarity	NPC223679
0.7083	Intermediate Similarity	NPC262747
0.7083	Intermediate Similarity	NPC473756
0.7077	Intermediate Similarity	NPC469723
0.7059	Intermediate Similarity	NPC329656
0.7059	Intermediate Similarity	NPC470693
0.7059	Intermediate Similarity	NPC22301
0.7049	Intermediate Similarity	NPC141699
0.7042	Intermediate Similarity	NPC244166
0.7042	Intermediate Similarity	NPC65650
0.7042	Intermediate Similarity	NPC329852
0.7031	Intermediate Similarity	NPC55376
0.7027	Intermediate Similarity	NPC472470
0.7027	Intermediate Similarity	NPC469802
0.7027	Intermediate Similarity	NPC474739
0.7027	Intermediate Similarity	NPC233332
0.7018	Intermediate Similarity	NPC207815
0.7018	Intermediate Similarity	NPC234597
0.7	Intermediate Similarity	NPC472018
0.7	Intermediate Similarity	NPC474543
0.7	Intermediate Similarity	NPC478120
0.7	Intermediate Similarity	NPC238425
0.6986	Remote Similarity	NPC474341
0.6986	Remote Similarity	NPC128276
0.6986	Remote Similarity	NPC471220
0.6986	Remote Similarity	NPC209135
0.6986	Remote Similarity	NPC474816
0.6984	Remote Similarity	NPC474267
0.6984	Remote Similarity	NPC82465
0.6984	Remote Similarity	NPC286189
0.697	Remote Similarity	NPC107258
0.6957	Remote Similarity	NPC475310
0.6957	Remote Similarity	NPC316029
0.6949	Remote Similarity	NPC216407
0.6944	Remote Similarity	NPC477202
0.6944	Remote Similarity	NPC235906
0.6935	Remote Similarity	NPC212730
0.6935	Remote Similarity	NPC265551
0.6935	Remote Similarity	NPC165808
0.6935	Remote Similarity	NPC135863
0.6933	Remote Similarity	NPC79277
0.6933	Remote Similarity	NPC25554
0.6933	Remote Similarity	NPC471325
0.6933	Remote Similarity	NPC14203
0.6933	Remote Similarity	NPC474894
0.6933	Remote Similarity	NPC112868
0.6933	Remote Similarity	NPC229584
0.6933	Remote Similarity	NPC475481
0.6912	Remote Similarity	NPC310210
0.6901	Remote Similarity	NPC470686
0.6901	Remote Similarity	NPC476355
0.6901	Remote Similarity	NPC20025
0.6897	Remote Similarity	NPC15789
0.6892	Remote Similarity	NPC471299
0.6892	Remote Similarity	NPC139712
0.6892	Remote Similarity	NPC469690
0.6892	Remote Similarity	NPC86971
0.6885	Remote Similarity	NPC223604
0.6885	Remote Similarity	NPC477984
0.6885	Remote Similarity	NPC478117
0.6875	Remote Similarity	NPC79756
0.6866	Remote Similarity	NPC259156
0.6866	Remote Similarity	NPC242945
0.6857	Remote Similarity	NPC316185
0.6849	Remote Similarity	NPC97516
0.6849	Remote Similarity	NPC57744
0.6849	Remote Similarity	NPC65603
0.6849	Remote Similarity	NPC40049
0.6849	Remote Similarity	NPC474760
0.6849	Remote Similarity	NPC41780
0.6849	Remote Similarity	NPC477203
0.6849	Remote Similarity	NPC315394
0.6849	Remote Similarity	NPC470240
0.6849	Remote Similarity	NPC187568
0.6849	Remote Similarity	NPC476794
0.6842	Remote Similarity	NPC35556
0.6842	Remote Similarity	NPC471218
0.6812	Remote Similarity	NPC107130
0.6806	Remote Similarity	NPC193351
0.6806	Remote Similarity	NPC138408
0.6806	Remote Similarity	NPC155587
0.6806	Remote Similarity	NPC226669
0.6774	Remote Similarity	NPC252860
0.6769	Remote Similarity	NPC317025
0.6769	Remote Similarity	NPC317177
0.6769	Remote Similarity	NPC326645
0.6769	Remote Similarity	NPC329416
0.6765	Remote Similarity	NPC21998
0.6765	Remote Similarity	NPC225272
0.6761	Remote Similarity	NPC58956
0.6761	Remote Similarity	NPC470237
0.6761	Remote Similarity	NPC269206
0.6761	Remote Similarity	NPC295633
0.6761	Remote Similarity	NPC276336
0.6757	Remote Similarity	NPC105197
0.6757	Remote Similarity	NPC253749
0.6757	Remote Similarity	NPC299235
0.6757	Remote Similarity	NPC184737
0.6753	Remote Similarity	NPC42476
0.6753	Remote Similarity	NPC472473
0.6753	Remote Similarity	NPC475947
0.6753	Remote Similarity	NPC170377
0.6753	Remote Similarity	NPC469

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 NPC96663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	2870
0.2-0.3	4168
0.3-0.4	1537
0.4-0.5	322
0.5-0.6	93
0.6-0.7	13
0.7-0.8	3
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.85	High Similarity	NPD5325	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6927	Phase 3
0.7286	Intermediate Similarity	NPD8039	Approved
0.6769	Remote Similarity	NPD4192	Approved
0.6769	Remote Similarity	NPD4191	Approved
0.6769	Remote Similarity	NPD4193	Approved
0.6769	Remote Similarity	NPD4194	Approved
0.6623	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6097	Approved
0.6607	Remote Similarity	NPD6096	Approved
0.6582	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5343	Approved
0.6456	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5209	Approved
0.6329	Remote Similarity	NPD7154	Phase 3
0.6265	Remote Similarity	NPD6051	Approved
0.625	Remote Similarity	NPD4219	Approved
0.619	Remote Similarity	NPD6698	Approved
0.619	Remote Similarity	NPD46	Approved
0.619	Remote Similarity	NPD7838	Discovery
0.6167	Remote Similarity	NPD4220	Pre-registration
0.6154	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD5362	Discontinued
0.6104	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD2268	Discontinued
0.5976	Remote Similarity	NPD1694	Approved
0.5976	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD28	Approved
0.5968	Remote Similarity	NPD29	Approved
0.5949	Remote Similarity	NPD4822	Approved
0.5949	Remote Similarity	NPD4820	Approved
0.5949	Remote Similarity	NPD4819	Approved
0.5949	Remote Similarity	NPD4821	Approved
0.5932	Remote Similarity	NPD4265	Approved
0.5932	Remote Similarity	NPD39	Approved
0.5926	Remote Similarity	NPD5332	Approved
0.5926	Remote Similarity	NPD5331	Approved
0.5897	Remote Similarity	NPD4271	Approved
0.5897	Remote Similarity	NPD4268	Approved
0.5882	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD4790	Discontinued
0.5846	Remote Similarity	NPD342	Phase 1
0.5814	Remote Similarity	NPD5785	Approved
0.5802	Remote Similarity	NPD4270	Approved
0.5802	Remote Similarity	NPD6435	Approved
0.5802	Remote Similarity	NPD4269	Approved
0.5797	Remote Similarity	NPD368	Approved
0.575	Remote Similarity	NPD4252	Approved
0.5747	Remote Similarity	NPD7637	Suspended
0.5747	Remote Similarity	NPD7983	Approved
0.5714	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD5783	Phase 3
0.5714	Remote Similarity	NPD7334	Approved
0.5714	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD6684	Approved
0.5714	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD5786	Approved
0.5698	Remote Similarity	NPD1695	Approved
0.5692	Remote Similarity	NPD4266	Approved
0.5692	Remote Similarity	NPD3194	Approved
0.5692	Remote Similarity	NPD3196	Approved
0.5692	Remote Similarity	NPD3195	Phase 2
0.5682	Remote Similarity	NPD5778	Approved
0.5682	Remote Similarity	NPD5779	Approved
0.5679	Remote Similarity	NPD5369	Approved
0.5667	Remote Similarity	NPD3174	Discontinued
0.5652	Remote Similarity	NPD6648	Approved
0.5652	Remote Similarity	NPD7639	Approved
0.5652	Remote Similarity	NPD7640	Approved
0.5647	Remote Similarity	NPD4250	Approved
0.5647	Remote Similarity	NPD4251	Approved
0.5636	Remote Similarity	NPD319	Phase 1

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