NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	350.138
LogP:	1.967
LogD:	1.331
LogS:	-3.423
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	6.25
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.342
MDCK Permeability:	1.5668290870962664e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.162
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.574
Plasma Protein Binding (PPB):	85.57998657226562%
Volume Distribution (VD):	0.43
Pgp-substrate:	17.98480224609375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.547
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.564
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.42
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	1.721
Half-life (T1/2):	0.621

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.673
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.149
Skin Sensitization:	0.408
Carcinogencity:	0.05
Eye Corrosion:	0.156
Eye Irritation:	0.391
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC477853

Natural Product ID:	NPC477853
*Common Name:**	(1R,4R,5R,8R,9S,10S,13S,14S)-8,14-dihydroxy-5,9,14-trimethyltetracyclo[11.2.1.01,10.04,9]hexadec-11-ene-5-carboxylic acid
IUPAC Name:	(1R,4R,5R,8R,9S,10S,13S,14S)-8,14-dihydroxy-5,9,14-trimethyltetracyclo[11.2.1.01,10.04,9]hexadec-11-ene-5-carboxylic acid
Synonyms:
Standard InCHIKey:	GNSDUTWQMBDEOG-SJVPJYLASA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-17(16(22)23)8-7-15(21)19(3)13(17)6-9-20-10-12(4-5-14(19)20)18(2,24)11-20/h4-5,12-15,21,24H,6-11H2,1-3H3,(H,22,23)/t12-,13+,14-,15-,17-,18+,19+,20-/m1/s1
SMILES:	C[C@]1(CC[C@H]([C@]2([C@H]1CC[C@@]34[C@@H]2C=C[C@H](C3)[C@@](C4)(C)O)C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46907076
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO33608	Rhizopus arrhizus	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20481544]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	10000	nM	PMID[20481544]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	10000	nM	PMID[20481544]

☑ 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 NPC477853 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	184
0.1-0.2	1181
0.2-0.3	4723
0.3-0.4	12613
0.4-0.5	9142
0.5-0.6	5955
0.6-0.7	5648
0.7-0.8	2881
0.8-0.85	320
0.85-0.9	45
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC477854
0.9348	High Similarity	NPC173272
0.9239	High Similarity	NPC48330
0.9149	High Similarity	NPC114274
0.9022	High Similarity	NPC477855
0.8842	High Similarity	NPC190554
0.8842	High Similarity	NPC108078
0.8817	High Similarity	NPC470375
0.8817	High Similarity	NPC470376
0.8817	High Similarity	NPC206810
0.8788	High Similarity	NPC231530
0.8788	High Similarity	NPC278628
0.8696	High Similarity	NPC474704
0.8696	High Similarity	NPC475921
0.8687	High Similarity	NPC477812
0.8687	High Similarity	NPC29705
0.8681	High Similarity	NPC474684
0.8681	High Similarity	NPC142361
0.8673	High Similarity	NPC193934
0.8673	High Similarity	NPC271980
0.866	High Similarity	NPC83709
0.866	High Similarity	NPC15390
0.8652	High Similarity	NPC477852
0.8632	High Similarity	NPC279974
0.8632	High Similarity	NPC472485
0.8632	High Similarity	NPC469599
0.8627	High Similarity	NPC197428
0.8614	High Similarity	NPC94529
0.8587	High Similarity	NPC242864
0.8586	High Similarity	NPC140723
0.8586	High Similarity	NPC191892
0.8571	High Similarity	NPC155011
0.8542	High Similarity	NPC49371
0.8526	High Similarity	NPC111015
0.8526	High Similarity	NPC166906
0.8515	High Similarity	NPC42847
0.8515	High Similarity	NPC44063
0.8515	High Similarity	NPC64844
0.8511	High Similarity	NPC23434
0.8511	High Similarity	NPC189520
0.85	High Similarity	NPC201763
0.85	High Similarity	NPC471293
0.8495	Intermediate Similarity	NPC128496
0.8485	Intermediate Similarity	NPC22388
0.8485	Intermediate Similarity	NPC477054
0.8478	Intermediate Similarity	NPC233836
0.8478	Intermediate Similarity	NPC159046
0.8478	Intermediate Similarity	NPC187376
0.8469	Intermediate Similarity	NPC218383
0.8469	Intermediate Similarity	NPC144956
0.8462	Intermediate Similarity	NPC280782
0.8462	Intermediate Similarity	NPC71348
0.8454	Intermediate Similarity	NPC18509
0.8438	Intermediate Similarity	NPC162001
0.8438	Intermediate Similarity	NPC317586
0.8438	Intermediate Similarity	NPC473240
0.8438	Intermediate Similarity	NPC222845
0.8438	Intermediate Similarity	NPC45324
0.8438	Intermediate Similarity	NPC470016
0.8416	Intermediate Similarity	NPC149047
0.8416	Intermediate Similarity	NPC196528
0.8404	Intermediate Similarity	NPC469400
0.8404	Intermediate Similarity	NPC471896
0.84	Intermediate Similarity	NPC222153
0.8387	Intermediate Similarity	NPC328539
0.8387	Intermediate Similarity	NPC193360
0.8384	Intermediate Similarity	NPC477051
0.8384	Intermediate Similarity	NPC477052
0.8384	Intermediate Similarity	NPC477053
0.837	Intermediate Similarity	NPC28252
0.837	Intermediate Similarity	NPC73038
0.837	Intermediate Similarity	NPC55309
0.8367	Intermediate Similarity	NPC186810
0.8367	Intermediate Similarity	NPC119036
0.8351	Intermediate Similarity	NPC305483
0.8351	Intermediate Similarity	NPC42042
0.8351	Intermediate Similarity	NPC95565
0.8351	Intermediate Similarity	NPC234564
0.8351	Intermediate Similarity	NPC328162
0.8351	Intermediate Similarity	NPC476318
0.8351	Intermediate Similarity	NPC96859
0.8351	Intermediate Similarity	NPC476327
0.835	Intermediate Similarity	NPC2766
0.8333	Intermediate Similarity	NPC263729
0.8333	Intermediate Similarity	NPC196485
0.8333	Intermediate Similarity	NPC475060
0.8333	Intermediate Similarity	NPC245972
0.8333	Intermediate Similarity	NPC220229
0.8333	Intermediate Similarity	NPC59530
0.8333	Intermediate Similarity	NPC470957
0.8333	Intermediate Similarity	NPC165873
0.8333	Intermediate Similarity	NPC470958
0.8317	Intermediate Similarity	NPC204833
0.8317	Intermediate Similarity	NPC209502
0.8316	Intermediate Similarity	NPC185936
0.8316	Intermediate Similarity	NPC110657
0.8316	Intermediate Similarity	NPC86266
0.8316	Intermediate Similarity	NPC212301
0.8316	Intermediate Similarity	NPC154101
0.8316	Intermediate Similarity	NPC26888
0.8316	Intermediate Similarity	NPC168027
0.8298	Intermediate Similarity	NPC476733
0.8298	Intermediate Similarity	NPC76879
0.8298	Intermediate Similarity	NPC474245
0.8298	Intermediate Similarity	NPC77168
0.8298	Intermediate Similarity	NPC102414
0.8298	Intermediate Similarity	NPC215029
0.8298	Intermediate Similarity	NPC186688
0.8298	Intermediate Similarity	NPC84271
0.8298	Intermediate Similarity	NPC32830
0.8283	Intermediate Similarity	NPC110149
0.8283	Intermediate Similarity	NPC316964
0.8283	Intermediate Similarity	NPC154072
0.828	Intermediate Similarity	NPC298904
0.8265	Intermediate Similarity	NPC320306
0.8265	Intermediate Similarity	NPC107243
0.8265	Intermediate Similarity	NPC57416
0.8265	Intermediate Similarity	NPC189880
0.8252	Intermediate Similarity	NPC163216
0.8252	Intermediate Similarity	NPC472218
0.8252	Intermediate Similarity	NPC472219
0.8252	Intermediate Similarity	NPC472217
0.8252	Intermediate Similarity	NPC217201
0.8247	Intermediate Similarity	NPC266899
0.8247	Intermediate Similarity	NPC472824
0.8247	Intermediate Similarity	NPC69548
0.8247	Intermediate Similarity	NPC184848
0.8235	Intermediate Similarity	NPC150531
0.8235	Intermediate Similarity	NPC48733
0.8235	Intermediate Similarity	NPC202167
0.8235	Intermediate Similarity	NPC319077
0.8235	Intermediate Similarity	NPC296945
0.8235	Intermediate Similarity	NPC257353
0.8235	Intermediate Similarity	NPC323834
0.8235	Intermediate Similarity	NPC97202
0.8235	Intermediate Similarity	NPC214264
0.8235	Intermediate Similarity	NPC302607
0.8235	Intermediate Similarity	NPC49958
0.8235	Intermediate Similarity	NPC50692
0.8235	Intermediate Similarity	NPC260268
0.8235	Intermediate Similarity	NPC476027
0.8235	Intermediate Similarity	NPC152695
0.8235	Intermediate Similarity	NPC85829
0.8235	Intermediate Similarity	NPC171137
0.8229	Intermediate Similarity	NPC470224
0.8229	Intermediate Similarity	NPC244356
0.8229	Intermediate Similarity	NPC224060
0.8229	Intermediate Similarity	NPC141497
0.8229	Intermediate Similarity	NPC107674
0.8229	Intermediate Similarity	NPC170220
0.8224	Intermediate Similarity	NPC270958
0.8222	Intermediate Similarity	NPC473420
0.8218	Intermediate Similarity	NPC312900
0.8218	Intermediate Similarity	NPC55872
0.8218	Intermediate Similarity	NPC159442
0.8218	Intermediate Similarity	NPC36688
0.8211	Intermediate Similarity	NPC148414
0.8211	Intermediate Similarity	NPC111585
0.8211	Intermediate Similarity	NPC320026
0.8211	Intermediate Similarity	NPC175628
0.8211	Intermediate Similarity	NPC289213
0.8208	Intermediate Similarity	NPC202889
0.8208	Intermediate Similarity	NPC962
0.8208	Intermediate Similarity	NPC250109
0.8208	Intermediate Similarity	NPC194100
0.82	Intermediate Similarity	NPC81530
0.8191	Intermediate Similarity	NPC328313
0.8191	Intermediate Similarity	NPC53911
0.8182	Intermediate Similarity	NPC260149
0.8182	Intermediate Similarity	NPC58942
0.8182	Intermediate Similarity	NPC197386
0.8182	Intermediate Similarity	NPC477813
0.8182	Intermediate Similarity	NPC48647
0.8173	Intermediate Similarity	NPC257082
0.8173	Intermediate Similarity	NPC11710
0.8173	Intermediate Similarity	NPC241927
0.8173	Intermediate Similarity	NPC10064
0.8173	Intermediate Similarity	NPC472216
0.8173	Intermediate Similarity	NPC284828
0.8173	Intermediate Similarity	NPC258543
0.8173	Intermediate Similarity	NPC173905
0.8173	Intermediate Similarity	NPC170221
0.8173	Intermediate Similarity	NPC5475
0.8173	Intermediate Similarity	NPC285298
0.8172	Intermediate Similarity	NPC20688
0.8172	Intermediate Similarity	NPC474970
0.8172	Intermediate Similarity	NPC82979
0.8163	Intermediate Similarity	NPC249954
0.8163	Intermediate Similarity	NPC253115
0.8163	Intermediate Similarity	NPC304899
0.8155	Intermediate Similarity	NPC472925
0.8155	Intermediate Similarity	NPC477916
0.8155	Intermediate Similarity	NPC83744
0.8152	Intermediate Similarity	NPC221758
0.8152	Intermediate Similarity	NPC127606
0.8152	Intermediate Similarity	NPC59453
0.8152	Intermediate Similarity	NPC82902
0.8152	Intermediate Similarity	NPC124172
0.8152	Intermediate Similarity	NPC475798
0.8144	Intermediate Similarity	NPC119562

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 NPC477853 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1502
0.2-0.3	3958
0.3-0.4	2354
0.4-0.5	648
0.5-0.6	182
0.6-0.7	162
0.7-0.8	130
0.8-0.85	51
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8515	High Similarity	NPD5697	Approved
0.8469	Intermediate Similarity	NPD5286	Approved
0.8469	Intermediate Similarity	NPD4696	Approved
0.8469	Intermediate Similarity	NPD5285	Approved
0.8454	Intermediate Similarity	NPD4755	Approved
0.8431	Intermediate Similarity	NPD6011	Approved
0.8431	Intermediate Similarity	NPD6881	Approved
0.8431	Intermediate Similarity	NPD6899	Approved
0.8416	Intermediate Similarity	NPD5739	Approved
0.8416	Intermediate Similarity	NPD7128	Approved
0.8416	Intermediate Similarity	NPD6675	Approved
0.8416	Intermediate Similarity	NPD6402	Approved
0.8384	Intermediate Similarity	NPD5223	Approved
0.8381	Intermediate Similarity	NPD4632	Approved
0.835	Intermediate Similarity	NPD6012	Approved
0.835	Intermediate Similarity	NPD6013	Approved
0.835	Intermediate Similarity	NPD6014	Approved
0.8333	Intermediate Similarity	NPD5701	Approved
0.8316	Intermediate Similarity	NPD6079	Approved
0.83	Intermediate Similarity	NPD4633	Approved
0.83	Intermediate Similarity	NPD5224	Approved
0.83	Intermediate Similarity	NPD5225	Approved
0.83	Intermediate Similarity	NPD5226	Approved
0.83	Intermediate Similarity	NPD5211	Phase 2
0.8298	Intermediate Similarity	NPD5328	Approved
0.8283	Intermediate Similarity	NPD4700	Approved
0.8269	Intermediate Similarity	NPD7290	Approved
0.8269	Intermediate Similarity	NPD7102	Approved
0.8269	Intermediate Similarity	NPD6883	Approved
0.8252	Intermediate Similarity	NPD7320	Approved
0.8235	Intermediate Similarity	NPD6008	Approved
0.8229	Intermediate Similarity	NPD4202	Approved
0.8218	Intermediate Similarity	NPD5174	Approved
0.8218	Intermediate Similarity	NPD5175	Approved
0.819	Intermediate Similarity	NPD6847	Approved
0.819	Intermediate Similarity	NPD6649	Approved
0.819	Intermediate Similarity	NPD6617	Approved
0.819	Intermediate Similarity	NPD8130	Phase 1
0.819	Intermediate Similarity	NPD6650	Approved
0.819	Intermediate Similarity	NPD6869	Approved
0.8173	Intermediate Similarity	NPD6372	Approved
0.8173	Intermediate Similarity	NPD6373	Approved
0.8163	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD5221	Approved
0.8163	Intermediate Similarity	NPD5222	Approved
0.8152	Intermediate Similarity	NPD4786	Approved
0.8148	Intermediate Similarity	NPD6009	Approved
0.8137	Intermediate Similarity	NPD5141	Approved
0.8132	Intermediate Similarity	NPD3667	Approved
0.8113	Intermediate Similarity	NPD8297	Approved
0.8113	Intermediate Similarity	NPD6882	Approved
0.8095	Intermediate Similarity	NPD4634	Approved
0.8081	Intermediate Similarity	NPD5173	Approved
0.8041	Intermediate Similarity	NPD6399	Phase 3
0.8039	Intermediate Similarity	NPD4754	Approved
0.8019	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD4697	Phase 3
0.7979	Intermediate Similarity	NPD3618	Phase 1
0.7957	Intermediate Similarity	NPD3665	Phase 1
0.7957	Intermediate Similarity	NPD3666	Approved
0.7957	Intermediate Similarity	NPD3133	Approved
0.7928	Intermediate Similarity	NPD6319	Approved
0.7917	Intermediate Similarity	NPD4753	Phase 2
0.7905	Intermediate Similarity	NPD4729	Approved
0.7905	Intermediate Similarity	NPD4730	Approved
0.79	Intermediate Similarity	NPD6083	Phase 2
0.79	Intermediate Similarity	NPD6084	Phase 2
0.7885	Intermediate Similarity	NPD4768	Approved
0.7885	Intermediate Similarity	NPD4767	Approved
0.7872	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5983	Phase 2
0.7822	Intermediate Similarity	NPD7638	Approved
0.7818	Intermediate Similarity	NPD6317	Approved
0.7757	Intermediate Similarity	NPD5247	Approved
0.7757	Intermediate Similarity	NPD5248	Approved
0.7757	Intermediate Similarity	NPD5249	Phase 3
0.7757	Intermediate Similarity	NPD5135	Approved
0.7757	Intermediate Similarity	NPD5169	Approved
0.7757	Intermediate Similarity	NPD5251	Approved
0.7757	Intermediate Similarity	NPD5250	Approved
0.7757	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5284	Approved
0.7755	Intermediate Similarity	NPD7515	Phase 2
0.7755	Intermediate Similarity	NPD5281	Approved
0.7748	Intermediate Similarity	NPD6335	Approved
0.7748	Intermediate Similarity	NPD6313	Approved
0.7748	Intermediate Similarity	NPD6314	Approved
0.7745	Intermediate Similarity	NPD7640	Approved
0.7745	Intermediate Similarity	NPD7639	Approved
0.7742	Intermediate Similarity	NPD4223	Phase 3
0.7742	Intermediate Similarity	NPD4221	Approved
0.7736	Intermediate Similarity	NPD5128	Approved
0.7727	Intermediate Similarity	NPD6274	Approved
0.7719	Intermediate Similarity	NPD7604	Phase 2
0.77	Intermediate Similarity	NPD4629	Approved
0.77	Intermediate Similarity	NPD5695	Phase 3
0.77	Intermediate Similarity	NPD5210	Approved
0.7692	Intermediate Similarity	NPD6115	Approved
0.7692	Intermediate Similarity	NPD6118	Approved
0.7692	Intermediate Similarity	NPD6114	Approved
0.7692	Intermediate Similarity	NPD6697	Approved
0.7685	Intermediate Similarity	NPD5216	Approved
0.7685	Intermediate Similarity	NPD5215	Approved
0.7685	Intermediate Similarity	NPD5217	Approved
0.7685	Intermediate Similarity	NPD5127	Approved
0.7679	Intermediate Similarity	NPD7101	Approved
0.7679	Intermediate Similarity	NPD7100	Approved
0.7667	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD7492	Approved
0.7647	Intermediate Similarity	NPD5696	Approved
0.7611	Intermediate Similarity	NPD6054	Approved
0.7604	Intermediate Similarity	NPD6409	Approved
0.7604	Intermediate Similarity	NPD5330	Approved
0.7604	Intermediate Similarity	NPD6684	Approved
0.7604	Intermediate Similarity	NPD7521	Approved
0.7604	Intermediate Similarity	NPD7334	Approved
0.7604	Intermediate Similarity	NPD7146	Approved
0.7586	Intermediate Similarity	NPD6616	Approved
0.7586	Intermediate Similarity	NPD6336	Discontinued
0.7579	Intermediate Similarity	NPD4197	Approved
0.7579	Intermediate Similarity	NPD3668	Phase 3
0.7544	Intermediate Similarity	NPD6016	Approved
0.7544	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6015	Approved
0.7527	Intermediate Similarity	NPD7525	Registered
0.7526	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7078	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.7478	Intermediate Similarity	NPD5988	Approved
0.7478	Intermediate Similarity	NPD6370	Approved
0.7477	Intermediate Similarity	NPD5167	Approved
0.7473	Intermediate Similarity	NPD6117	Approved
0.7458	Intermediate Similarity	NPD7736	Approved
0.7456	Intermediate Similarity	NPD6059	Approved
0.7449	Intermediate Similarity	NPD6903	Approved
0.7449	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7748	Approved
0.7423	Intermediate Similarity	NPD4689	Approved
0.7423	Intermediate Similarity	NPD5690	Phase 2
0.7423	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4138	Approved
0.7423	Intermediate Similarity	NPD6098	Approved
0.7423	Intermediate Similarity	NPD4690	Approved
0.7423	Intermediate Similarity	NPD4688	Approved
0.7423	Intermediate Similarity	NPD4693	Phase 3
0.7423	Intermediate Similarity	NPD5205	Approved
0.7411	Intermediate Similarity	NPD6868	Approved
0.7407	Intermediate Similarity	NPD5168	Approved
0.74	Intermediate Similarity	NPD8035	Phase 2
0.74	Intermediate Similarity	NPD6411	Approved
0.74	Intermediate Similarity	NPD8034	Phase 2
0.7391	Intermediate Similarity	NPD6116	Phase 1
0.7391	Intermediate Similarity	NPD6909	Approved
0.7391	Intermediate Similarity	NPD6908	Approved
0.7374	Intermediate Similarity	NPD6904	Approved
0.7374	Intermediate Similarity	NPD6080	Approved
0.7374	Intermediate Similarity	NPD6673	Approved
0.7373	Intermediate Similarity	NPD8293	Discontinued
0.7363	Intermediate Similarity	NPD6942	Approved
0.7363	Intermediate Similarity	NPD3703	Phase 2
0.7363	Intermediate Similarity	NPD7339	Approved
0.7347	Intermediate Similarity	NPD3573	Approved
0.7345	Intermediate Similarity	NPD7115	Discovery
0.734	Intermediate Similarity	NPD5368	Approved
0.7297	Intermediate Similarity	NPD6053	Discontinued
0.7292	Intermediate Similarity	NPD4788	Approved
0.7288	Intermediate Similarity	NPD7507	Approved
0.7273	Intermediate Similarity	NPD5737	Approved
0.7273	Intermediate Similarity	NPD5208	Approved
0.7273	Intermediate Similarity	NPD6672	Approved
0.7263	Intermediate Similarity	NPD5369	Approved
0.7255	Intermediate Similarity	NPD6001	Approved
0.7253	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4785	Approved
0.7253	Intermediate Similarity	NPD4784	Approved
0.7245	Intermediate Similarity	NPD5280	Approved
0.7245	Intermediate Similarity	NPD5279	Phase 3
0.7245	Intermediate Similarity	NPD4694	Approved
0.7234	Intermediate Similarity	NPD4195	Approved
0.7228	Intermediate Similarity	NPD5693	Phase 1
0.7228	Intermediate Similarity	NPD5694	Approved
0.7212	Intermediate Similarity	NPD7902	Approved
0.72	Intermediate Similarity	NPD6101	Approved
0.72	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6435	Approved
0.7174	Intermediate Similarity	NPD3702	Approved
0.7158	Intermediate Similarity	NPD4748	Discontinued
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD5778	Approved
0.7156	Intermediate Similarity	NPD6412	Phase 2
0.7129	Intermediate Similarity	NPD5207	Approved
0.7129	Intermediate Similarity	NPD5692	Phase 3
0.7128	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5362	Discontinued
0.7107	Intermediate Similarity	NPD7319	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7083	Intermediate Similarity	NPD4139	Approved
0.7083	Intermediate Similarity	NPD4692	Approved
0.7071	Intermediate Similarity	NPD5786	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