NPASS Compound

Structure

NPC329698 OpenBabel07101718312D 24 24 0 0 1 0 0 0 0 0999 V2000 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 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 -1.7321 2.0000 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 -3.4641 5.0000 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 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 8.0000 0.0000 O 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 17 1 0 0 0 0 2 18 1 0 0 0 0 4 20 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 22 1 0 0 0 0 16 24 1 0 0 0 0 19 3 1 6 0 0 0 19 21 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 13 1 6 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.3
Volume:	392.819
LogP:	7.373
LogD:	5.73
LogS:	-6.563
# Rotatable Bonds:	10
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.353
Synthetic Accessibility Score:	3.797
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.647
MDCK Permeability:	1.3125933946867008e-05
Pgp-inhibitor:	0.955
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.613
Plasma Protein Binding (PPB):	98.01367950439453%
Volume Distribution (VD):	1.583
Pgp-substrate:	2.600878953933716%

ADMET: Metabolism

CYP1A2-inhibitor:	0.271
CYP1A2-substrate:	0.311
CYP2C19-inhibitor:	0.345
CYP2C19-substrate:	0.48
CYP2C9-inhibitor:	0.367
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.295
CYP2D6-substrate:	0.224
CYP3A4-inhibitor:	0.589
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	4.366
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.492
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.966
Carcinogencity:	0.059
Eye Corrosion:	0.811
Eye Irritation:	0.758
Respiratory Toxicity:	0.583

Download Data

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

Natural Product: NPC329698

Natural Product ID:	NPC329698
*Common Name:**	Cassipouryl Acetate
IUPAC Name:	[(E)-3,7-dimethyl-9-[(1S,6S)-2,2,6-trimethylcyclohexyl]non-2-enyl] acetate
Synonyms:	Cassipouryl Acetate
Standard InCHIKey:	UMBAAYHFKZFIKK-RDFGKNDZSA-N
Standard InCHI:	InChI=1S/C22H40O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h14,17,19,21H,7-13,15-16H2,1-6H3/b18-14+/t17?,19-,21-/m0/s1
SMILES:	CC(CC[C@H]1[C@@H](C)CCCC1(C)C)CCC/C(=C/COC(=O)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479281
PubChem CID:	11588070
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001606] Retinoids

*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
NPO25743	Cassipourea madagascariensis	Species	Rhizophoraceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[16499334]
NPO25743	Cassipourea madagascariensis	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	2.8	ug.mL-1	PMID[545346]

☑ 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 NPC329698 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	145
0.1-0.2	1838
0.2-0.3	10330
0.3-0.4	15185
0.4-0.5	8058
0.5-0.6	5706
0.6-0.7	1305
0.7-0.8	121
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC185587
0.8814	High Similarity	NPC96663
0.873	High Similarity	NPC226066
0.8169	Intermediate Similarity	NPC4509
0.8116	Intermediate Similarity	NPC181587
0.8082	Intermediate Similarity	NPC242767
0.803	Intermediate Similarity	NPC107258
0.8028	Intermediate Similarity	NPC65650
0.7973	Intermediate Similarity	NPC233332
0.7973	Intermediate Similarity	NPC469802
0.791	Intermediate Similarity	NPC259156
0.791	Intermediate Similarity	NPC242945
0.7887	Intermediate Similarity	NPC20025
0.7879	Intermediate Similarity	NPC34883
0.7867	Intermediate Similarity	NPC229584
0.7867	Intermediate Similarity	NPC14203
0.7867	Intermediate Similarity	NPC25554
0.7857	Intermediate Similarity	NPC257618
0.7778	Intermediate Similarity	NPC11130
0.7763	Intermediate Similarity	NPC471218
0.7746	Intermediate Similarity	NPC476490
0.7746	Intermediate Similarity	NPC476489
0.7746	Intermediate Similarity	NPC222244
0.7746	Intermediate Similarity	NPC16349
0.7703	Intermediate Similarity	NPC105197
0.7681	Intermediate Similarity	NPC476945
0.7662	Intermediate Similarity	NPC23748
0.7662	Intermediate Similarity	NPC477124
0.7662	Intermediate Similarity	NPC472440
0.7662	Intermediate Similarity	NPC49208
0.7662	Intermediate Similarity	NPC469
0.7662	Intermediate Similarity	NPC42476
0.7639	Intermediate Similarity	NPC104644
0.76	Intermediate Similarity	NPC190211
0.7564	Intermediate Similarity	NPC318515
0.7564	Intermediate Similarity	NPC96055
0.7536	Intermediate Similarity	NPC472266
0.7534	Intermediate Similarity	NPC228978
0.7532	Intermediate Similarity	NPC268122
0.7532	Intermediate Similarity	NPC94200
0.7532	Intermediate Similarity	NPC200513
0.7532	Intermediate Similarity	NPC16321
0.75	Intermediate Similarity	NPC195424
0.75	Intermediate Similarity	NPC276336
0.75	Intermediate Similarity	NPC144947
0.7468	Intermediate Similarity	NPC30984
0.7468	Intermediate Similarity	NPC474013
0.7468	Intermediate Similarity	NPC472442
0.7468	Intermediate Similarity	NPC329630
0.7468	Intermediate Similarity	NPC35933
0.7467	Intermediate Similarity	NPC184737
0.7465	Intermediate Similarity	NPC469660
0.7436	Intermediate Similarity	NPC118423
0.7436	Intermediate Similarity	NPC474193
0.7436	Intermediate Similarity	NPC12283
0.7436	Intermediate Similarity	NPC311070
0.7432	Intermediate Similarity	NPC27205
0.7424	Intermediate Similarity	NPC19241
0.7403	Intermediate Similarity	NPC40228
0.7403	Intermediate Similarity	NPC170303
0.7375	Intermediate Similarity	NPC220478
0.7375	Intermediate Similarity	NPC118266
0.7361	Intermediate Similarity	NPC472254
0.7342	Intermediate Similarity	NPC470800
0.7342	Intermediate Similarity	NPC475100
0.7342	Intermediate Similarity	NPC149869
0.7333	Intermediate Similarity	NPC473756
0.7333	Intermediate Similarity	NPC262747
0.7333	Intermediate Similarity	NPC189206
0.7324	Intermediate Similarity	NPC101622
0.7324	Intermediate Similarity	NPC269841
0.7308	Intermediate Similarity	NPC256112
0.7288	Intermediate Similarity	NPC197467
0.7286	Intermediate Similarity	NPC474477
0.7284	Intermediate Similarity	NPC166857
0.7273	Intermediate Similarity	NPC268827
0.726	Intermediate Similarity	NPC135703
0.725	Intermediate Similarity	NPC65661
0.725	Intermediate Similarity	NPC471795
0.725	Intermediate Similarity	NPC86316
0.725	Intermediate Similarity	NPC42586
0.725	Intermediate Similarity	NPC106416
0.725	Intermediate Similarity	NPC473251
0.725	Intermediate Similarity	NPC189311
0.725	Intermediate Similarity	NPC217394
0.7237	Intermediate Similarity	NPC471220
0.7237	Intermediate Similarity	NPC239098
0.7237	Intermediate Similarity	NPC209135
0.7237	Intermediate Similarity	NPC474005
0.7237	Intermediate Similarity	NPC4827
0.7237	Intermediate Similarity	NPC474816
0.7222	Intermediate Similarity	NPC4299
0.7215	Intermediate Similarity	NPC22611
0.7215	Intermediate Similarity	NPC476927
0.7215	Intermediate Similarity	NPC474790
0.7215	Intermediate Similarity	NPC30502
0.7215	Intermediate Similarity	NPC222358
0.7215	Intermediate Similarity	NPC474976
0.7215	Intermediate Similarity	NPC193198
0.7206	Intermediate Similarity	NPC283247
0.72	Intermediate Similarity	NPC476317
0.72	Intermediate Similarity	NPC19907
0.7195	Intermediate Similarity	NPC474629
0.7195	Intermediate Similarity	NPC24816
0.7195	Intermediate Similarity	NPC473879
0.7195	Intermediate Similarity	NPC93411
0.7162	Intermediate Similarity	NPC166797
0.7162	Intermediate Similarity	NPC474524
0.7162	Intermediate Similarity	NPC475517
0.716	Intermediate Similarity	NPC168248
0.716	Intermediate Similarity	NPC286153
0.716	Intermediate Similarity	NPC102996
0.716	Intermediate Similarity	NPC329692
0.716	Intermediate Similarity	NPC471219
0.716	Intermediate Similarity	NPC131813
0.7143	Intermediate Similarity	NPC100906
0.7143	Intermediate Similarity	NPC44083
0.7143	Intermediate Similarity	NPC153987
0.7143	Intermediate Similarity	NPC471299
0.7143	Intermediate Similarity	NPC325869
0.7143	Intermediate Similarity	NPC327674
0.7143	Intermediate Similarity	NPC116013
0.7125	Intermediate Similarity	NPC474359
0.7125	Intermediate Similarity	NPC102048
0.7125	Intermediate Similarity	NPC471302
0.7125	Intermediate Similarity	NPC306951
0.7123	Intermediate Similarity	NPC133253
0.7123	Intermediate Similarity	NPC477084
0.7119	Intermediate Similarity	NPC47946
0.7119	Intermediate Similarity	NPC26600
0.7108	Intermediate Similarity	NPC284561
0.7108	Intermediate Similarity	NPC471654
0.7108	Intermediate Similarity	NPC174342
0.7108	Intermediate Similarity	NPC177141
0.7108	Intermediate Similarity	NPC246028
0.7108	Intermediate Similarity	NPC293044
0.7108	Intermediate Similarity	NPC474844
0.7105	Intermediate Similarity	NPC316500
0.7105	Intermediate Similarity	NPC283619
0.7105	Intermediate Similarity	NPC54996
0.7101	Intermediate Similarity	NPC469723
0.7101	Intermediate Similarity	NPC52449
0.7101	Intermediate Similarity	NPC169275
0.7083	Intermediate Similarity	NPC22301
0.7073	Intermediate Similarity	NPC476600
0.7073	Intermediate Similarity	NPC125925
0.7073	Intermediate Similarity	NPC102640
0.7073	Intermediate Similarity	NPC471796
0.7059	Intermediate Similarity	NPC317025
0.7059	Intermediate Similarity	NPC329416
0.7059	Intermediate Similarity	NPC326645
0.7059	Intermediate Similarity	NPC60565
0.7059	Intermediate Similarity	NPC317177
0.7051	Intermediate Similarity	NPC281880
0.7051	Intermediate Similarity	NPC472470
0.7042	Intermediate Similarity	NPC68703
0.7042	Intermediate Similarity	NPC69649
0.7027	Intermediate Similarity	NPC130016
0.7027	Intermediate Similarity	NPC56747
0.7027	Intermediate Similarity	NPC109576
0.7027	Intermediate Similarity	NPC180015
0.7024	Intermediate Similarity	NPC101651
0.7024	Intermediate Similarity	NPC273199
0.7024	Intermediate Similarity	NPC159748
0.7024	Intermediate Similarity	NPC78973
0.7024	Intermediate Similarity	NPC471818
0.7015	Intermediate Similarity	NPC309825
0.7013	Intermediate Similarity	NPC470052
0.7	Intermediate Similarity	NPC472377
0.6988	Remote Similarity	NPC472810
0.6988	Remote Similarity	NPC69713
0.6988	Remote Similarity	NPC106332
0.6988	Remote Similarity	NPC196407
0.6988	Remote Similarity	NPC472809
0.6988	Remote Similarity	NPC226863
0.6988	Remote Similarity	NPC477128
0.6986	Remote Similarity	NPC37929
0.6986	Remote Similarity	NPC64234
0.6974	Remote Similarity	NPC899
0.6974	Remote Similarity	NPC474463
0.6962	Remote Similarity	NPC108476
0.6962	Remote Similarity	NPC142163
0.6962	Remote Similarity	NPC327002
0.6962	Remote Similarity	NPC159148
0.6962	Remote Similarity	NPC195334
0.6962	Remote Similarity	NPC290495
0.6962	Remote Similarity	NPC475944
0.6957	Remote Similarity	NPC217940
0.6957	Remote Similarity	NPC155849
0.6944	Remote Similarity	NPC276290
0.6941	Remote Similarity	NPC234335
0.6941	Remote Similarity	NPC329842
0.6941	Remote Similarity	NPC177641
0.6941	Remote Similarity	NPC477122
0.6935	Remote Similarity	NPC289388
0.6933	Remote Similarity	NPC238146
0.6933	Remote Similarity	NPC477204
0.6933	Remote Similarity	NPC306928
0.6933	Remote Similarity	NPC75485
0.6933	Remote Similarity	NPC474758

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 NPC329698 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	2077
0.2-0.3	4461
0.3-0.4	1845
0.4-0.5	425
0.5-0.6	184
0.6-0.7	21
0.7-0.8	2
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
0.873	High Similarity	NPD5325	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD8039	Approved
0.7532	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6051	Approved
0.7097	Intermediate Similarity	NPD6927	Phase 3
0.7059	Intermediate Similarity	NPD4191	Approved
0.7059	Intermediate Similarity	NPD4192	Approved
0.7059	Intermediate Similarity	NPD4193	Approved
0.7059	Intermediate Similarity	NPD4194	Approved
0.6707	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4219	Approved
0.6548	Remote Similarity	NPD7146	Approved
0.6548	Remote Similarity	NPD7521	Approved
0.6548	Remote Similarity	NPD7334	Approved
0.6548	Remote Similarity	NPD6684	Approved
0.6548	Remote Similarity	NPD5330	Approved
0.6548	Remote Similarity	NPD6409	Approved
0.6484	Remote Similarity	NPD7638	Approved
0.6463	Remote Similarity	NPD5209	Approved
0.6429	Remote Similarity	NPD1694	Approved
0.6413	Remote Similarity	NPD7639	Approved
0.6413	Remote Similarity	NPD7640	Approved
0.6395	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5737	Approved
0.6395	Remote Similarity	NPD6672	Approved
0.6395	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD7637	Suspended
0.6304	Remote Similarity	NPD4225	Approved
0.6235	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD8264	Approved
0.6184	Remote Similarity	NPD4137	Phase 3
0.618	Remote Similarity	NPD5693	Phase 1
0.6173	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6098	Approved
0.6111	Remote Similarity	NPD6399	Phase 3
0.6104	Remote Similarity	NPD4747	Approved
0.6104	Remote Similarity	NPD4691	Approved
0.6076	Remote Similarity	NPD5733	Approved
0.6066	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7900	Approved
0.6044	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7748	Approved
0.6026	Remote Similarity	NPD5276	Approved
0.5976	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD6923	Approved
0.5974	Remote Similarity	NPD6922	Approved
0.596	Remote Similarity	NPD6686	Approved
0.5955	Remote Similarity	NPD6080	Approved
0.5955	Remote Similarity	NPD6904	Approved
0.5955	Remote Similarity	NPD6673	Approved
0.5915	Remote Similarity	NPD287	Approved
0.5909	Remote Similarity	NPD3573	Approved
0.5904	Remote Similarity	NPD7645	Phase 2
0.5897	Remote Similarity	NPD7144	Approved
0.5897	Remote Similarity	NPD7143	Approved
0.5895	Remote Similarity	NPD6648	Approved
0.5889	Remote Similarity	NPD5785	Approved
0.5889	Remote Similarity	NPD46	Approved
0.5889	Remote Similarity	NPD6698	Approved
0.5875	Remote Similarity	NPD4687	Approved
0.5875	Remote Similarity	NPD6926	Approved
0.5875	Remote Similarity	NPD4058	Approved
0.5875	Remote Similarity	NPD6924	Approved
0.5873	Remote Similarity	NPD6096	Approved
0.5873	Remote Similarity	NPD6097	Approved
0.5862	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6925	Approved
0.5854	Remote Similarity	NPD5776	Phase 2
0.5851	Remote Similarity	NPD6084	Phase 2
0.5851	Remote Similarity	NPD6083	Phase 2
0.5851	Remote Similarity	NPD7902	Approved
0.5846	Remote Similarity	NPD5343	Approved
0.5843	Remote Similarity	NPD5208	Approved
0.5833	Remote Similarity	NPD7514	Phase 3
0.5833	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7332	Phase 2
0.5833	Remote Similarity	NPD5344	Discontinued
0.5824	Remote Similarity	NPD6050	Approved
0.5824	Remote Similarity	NPD7515	Phase 2
0.5824	Remote Similarity	NPD6411	Approved
0.5823	Remote Similarity	NPD7150	Approved
0.5823	Remote Similarity	NPD7152	Approved
0.5823	Remote Similarity	NPD7151	Approved
0.5814	Remote Similarity	NPD7154	Phase 3
0.5814	Remote Similarity	NPD5362	Discontinued
0.5814	Remote Similarity	NPD6695	Phase 3
0.5806	Remote Similarity	NPD5695	Phase 3
0.5806	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6942	Approved
0.5802	Remote Similarity	NPD7339	Approved
0.5783	Remote Similarity	NPD7145	Approved
0.5773	Remote Similarity	NPD7632	Discontinued
0.5765	Remote Similarity	NPD6902	Approved
0.5761	Remote Similarity	NPD5778	Approved
0.5761	Remote Similarity	NPD5779	Approved
0.5758	Remote Similarity	NPD8262	Approved
0.5747	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD4786	Approved
0.5745	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD6933	Approved
0.5714	Remote Similarity	NPD5692	Phase 3
0.5714	Remote Similarity	NPD6929	Approved
0.5714	Remote Similarity	NPD5207	Approved
0.5714	Remote Similarity	NPD7838	Discovery
0.5698	Remote Similarity	NPD3667	Approved
0.5676	Remote Similarity	NPD368	Approved
0.5663	Remote Similarity	NPD6932	Approved
0.5652	Remote Similarity	NPD5694	Approved
0.5647	Remote Similarity	NPD6931	Approved
0.5647	Remote Similarity	NPD4822	Approved
0.5647	Remote Similarity	NPD6930	Phase 2
0.5647	Remote Similarity	NPD4820	Approved
0.5647	Remote Similarity	NPD7525	Registered
0.5647	Remote Similarity	NPD4821	Approved
0.5647	Remote Similarity	NPD4819	Approved
0.5638	Remote Similarity	NPD6049	Phase 2
0.5638	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD5332	Approved
0.5632	Remote Similarity	NPD5331	Approved
0.5625	Remote Similarity	NPD5696	Approved
0.5625	Remote Similarity	NPD4243	Approved
0.5604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD6101	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