NPASS Compound

Structure

NPC297265 OpenBabel07101719152D 35 38 0 0 1 0 0 0 0 0999 V2000 -2.6325 7.5306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9504 4.9563 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 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1583 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0574 1.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0209 8.2509 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 -1.7321 3.0000 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 -2.5981 3.5000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7914 6.2435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 4.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5835 7.2216 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2072 4.2872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0483 5.5743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 2 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 0.5000 0.0000 C 0 0 1 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 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3267 7.8907 0.0000 C 0 0 0 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 -4.4152 3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0972 5.8833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1187 8.8689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2777 7.5817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 8 35 1 0 0 0 0 9 11 1 0 0 0 0 9 23 2 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 25 2 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 1 1 6 0 0 0 19 27 1 0 0 0 0 20 2 1 6 0 0 0 20 29 1 0 0 0 0 21 32 2 0 0 0 0 22 23 1 0 0 0 0 22 30 1 1 0 0 0 23 31 1 0 0 0 0 24 28 1 0 0 0 0 24 30 1 6 0 0 0 25 29 1 0 0 0 0 25 31 1 0 0 0 0 26 28 1 0 0 0 0 26 33 1 1 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 29 5 1 6 0 0 0 30 6 1 6 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.36
Volume:	535.121
LogP:	4.993
LogD:	4.376
LogS:	-4.464
# Rotatable Bonds:	7
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	5.149
Fsp3:	0.806
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.899
MDCK Permeability:	1.630408769415226e-05
Pgp-inhibitor:	0.917
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.26
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.936
Plasma Protein Binding (PPB):	60.3922119140625%
Volume Distribution (VD):	1.513
Pgp-substrate:	27.129199981689453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.433
CYP2C19-inhibitor:	0.197
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.307
CYP2C9-substrate:	0.13
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.925
CYP3A4-substrate:	0.727

ADMET: Excretion

Clearance (CL):	6.657
Half-life (T1/2):	0.039

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.086
Carcinogencity:	0.204
Eye Corrosion:	0.01
Eye Irritation:	0.084
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC297265

Natural Product ID:	NPC297265
*Common Name:**	Neoabiestrine C
IUPAC Name:	methyl (2R,6R)-6-[(3R,5R,9S,10R,14S,17S)-3-hydroxy-4,4,10,14,17-pentamethyl-2,3,5,6,9,11,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoate
Synonyms:
Standard InCHIKey:	FHEFPQNFQGYGPO-VHTZULEWSA-N
Standard InCHI:	InChI=1S/C31H48O4/c1-19(27(34)35-8)17-21(32)18-20(2)29(5)15-16-31(7)23-9-11-24-28(3,4)26(33)13-14-30(24,6)22(23)10-12-25(29)31/h9,12,19-20,22,24,26,33H,10-11,13-18H2,1-8H3/t19-,20-,22-,24+,26-,29+,30-,31+/m1/s1
SMILES:	C[C@H](CC(=O)C[C@@H](C)[C@]1(C)CC[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](CC[C@]4(C)[C@@H]3CC=C12)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3353858
PubChem CID:	66560962
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO33399	abies faxoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25554367]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[527298]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	50000.0	nM	PMID[527298]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[527298]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[527298]

☑ 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 NPC297265 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	164
0.1-0.2	1050
0.2-0.3	4621
0.3-0.4	13531
0.4-0.5	9038
0.5-0.6	5930
0.6-0.7	5445
0.7-0.8	2529
0.8-0.85	272
0.85-0.9	90
0.9-0.95	26
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9432	High Similarity	NPC170220
0.9432	High Similarity	NPC107674
0.9432	High Similarity	NPC141497
0.9318	High Similarity	NPC212301
0.9318	High Similarity	NPC86266
0.9318	High Similarity	NPC110657
0.9302	High Similarity	NPC187376
0.9302	High Similarity	NPC233836
0.9302	High Similarity	NPC159046
0.9205	High Similarity	NPC175628
0.9205	High Similarity	NPC111585
0.9205	High Similarity	NPC148414
0.9195	High Similarity	NPC242864
0.9186	High Similarity	NPC28252
0.9186	High Similarity	NPC55309
0.9111	High Similarity	NPC159410
0.9111	High Similarity	NPC49670
0.9101	High Similarity	NPC23434
0.9101	High Similarity	NPC26888
0.9091	High Similarity	NPC77168
0.9091	High Similarity	NPC475921
0.9091	High Similarity	NPC474889
0.9091	High Similarity	NPC84271
0.9091	High Similarity	NPC102414
0.9091	High Similarity	NPC474704
0.908	High Similarity	NPC474684
0.908	High Similarity	NPC142361
0.9011	High Similarity	NPC470016
0.9011	High Similarity	NPC162001
0.9011	High Similarity	NPC184848
0.9011	High Similarity	NPC45324
0.9011	High Similarity	NPC222845
0.9011	High Similarity	NPC317586
0.9011	High Similarity	NPC69548
0.9	High Similarity	NPC470224
0.9	High Similarity	NPC470375
0.9	High Similarity	NPC470376
0.8989	High Similarity	NPC471896
0.8989	High Similarity	NPC469400
0.8966	High Similarity	NPC73038
0.8925	High Similarity	NPC477813
0.8901	High Similarity	NPC166906
0.8901	High Similarity	NPC469406
0.8889	High Similarity	NPC154101
0.8889	High Similarity	NPC189520
0.8876	High Similarity	NPC54689
0.8842	High Similarity	NPC234892
0.8804	High Similarity	NPC469599
0.8804	High Similarity	NPC473648
0.8804	High Similarity	NPC255809
0.8791	High Similarity	NPC152897
0.8791	High Similarity	NPC470254
0.8791	High Similarity	NPC66429
0.8778	High Similarity	NPC291028
0.8764	High Similarity	NPC471722
0.8764	High Similarity	NPC294480
0.875	High Similarity	NPC325594
0.875	High Similarity	NPC94755
0.875	High Similarity	NPC72133
0.875	High Similarity	NPC155011
0.8737	High Similarity	NPC473514
0.8723	High Similarity	NPC186810
0.8723	High Similarity	NPC48647
0.8721	High Similarity	NPC133391
0.871	High Similarity	NPC96859
0.871	High Similarity	NPC120708
0.871	High Similarity	NPC305483
0.871	High Similarity	NPC328162
0.871	High Similarity	NPC173272
0.871	High Similarity	NPC95565
0.8681	High Similarity	NPC107690
0.8681	High Similarity	NPC105189
0.8667	High Similarity	NPC86319
0.8667	High Similarity	NPC275740
0.8652	High Similarity	NPC96496
0.8652	High Similarity	NPC312215
0.8652	High Similarity	NPC167877
0.8646	High Similarity	NPC136289
0.8646	High Similarity	NPC293753
0.8632	High Similarity	NPC88198
0.8632	High Similarity	NPC299971
0.8632	High Similarity	NPC144660
0.8632	High Similarity	NPC316964
0.8632	High Similarity	NPC51370
0.8617	High Similarity	NPC108078
0.8617	High Similarity	NPC320306
0.8605	High Similarity	NPC473420
0.8605	High Similarity	NPC38350
0.8605	High Similarity	NPC201912
0.8602	High Similarity	NPC139459
0.8602	High Similarity	NPC48330
0.8602	High Similarity	NPC263347
0.8602	High Similarity	NPC279974
0.8587	High Similarity	NPC295643
0.8587	High Similarity	NPC272075
0.8587	High Similarity	NPC243866
0.8587	High Similarity	NPC214756
0.8587	High Similarity	NPC474436
0.8587	High Similarity	NPC49776
0.8587	High Similarity	NPC63118
0.8571	High Similarity	NPC477149
0.8571	High Similarity	NPC477872
0.8571	High Similarity	NPC191684
0.8571	High Similarity	NPC7260
0.8571	High Similarity	NPC273621
0.8571	High Similarity	NPC120968
0.8571	High Similarity	NPC477147
0.8571	High Similarity	NPC193750
0.8571	High Similarity	NPC227467
0.8571	High Similarity	NPC20388
0.8571	High Similarity	NPC44240
0.8571	High Similarity	NPC18872
0.8571	High Similarity	NPC210037
0.8571	High Similarity	NPC290614
0.8557	High Similarity	NPC236390
0.8556	High Similarity	NPC52169
0.8556	High Similarity	NPC183546
0.8556	High Similarity	NPC40552
0.8556	High Similarity	NPC143767
0.8556	High Similarity	NPC182797
0.8556	High Similarity	NPC131470
0.8556	High Similarity	NPC246708
0.8556	High Similarity	NPC471724
0.8556	High Similarity	NPC474719
0.8542	High Similarity	NPC81530
0.8539	High Similarity	NPC6979
0.8539	High Similarity	NPC322159
0.8539	High Similarity	NPC474970
0.8539	High Similarity	NPC212843
0.8526	High Similarity	NPC16021
0.8526	High Similarity	NPC478056
0.8523	High Similarity	NPC221758
0.8523	High Similarity	NPC59453
0.8523	High Similarity	NPC473246
0.8523	High Similarity	NPC165064
0.8511	High Similarity	NPC7124
0.8511	High Similarity	NPC155676
0.8511	High Similarity	NPC328371
0.8511	High Similarity	NPC472941
0.8511	High Similarity	NPC456
0.8506	High Similarity	NPC260956
0.8506	High Similarity	NPC240302
0.8506	High Similarity	NPC73882
0.8495	Intermediate Similarity	NPC471720
0.8478	Intermediate Similarity	NPC187722
0.8478	Intermediate Similarity	NPC4036
0.8478	Intermediate Similarity	NPC65120
0.8478	Intermediate Similarity	NPC474525
0.8478	Intermediate Similarity	NPC38754
0.8478	Intermediate Similarity	NPC158030
0.8478	Intermediate Similarity	NPC145067
0.8478	Intermediate Similarity	NPC233455
0.8469	Intermediate Similarity	NPC96268
0.8462	Intermediate Similarity	NPC61543
0.8462	Intermediate Similarity	NPC225585
0.8462	Intermediate Similarity	NPC474570
0.8462	Intermediate Similarity	NPC234346
0.8462	Intermediate Similarity	NPC214387
0.8462	Intermediate Similarity	NPC128496
0.8462	Intermediate Similarity	NPC59263
0.8462	Intermediate Similarity	NPC1015
0.8462	Intermediate Similarity	NPC25906
0.8462	Intermediate Similarity	NPC143232
0.8462	Intermediate Similarity	NPC270768
0.8462	Intermediate Similarity	NPC31985
0.8462	Intermediate Similarity	NPC198664
0.8462	Intermediate Similarity	NPC290972
0.8462	Intermediate Similarity	NPC274330
0.8462	Intermediate Similarity	NPC32830
0.8462	Intermediate Similarity	NPC121798
0.8462	Intermediate Similarity	NPC263393
0.8462	Intermediate Similarity	NPC130520
0.8462	Intermediate Similarity	NPC474245
0.8462	Intermediate Similarity	NPC293048
0.8462	Intermediate Similarity	NPC127689
0.8462	Intermediate Similarity	NPC64872
0.8462	Intermediate Similarity	NPC470588
0.8454	Intermediate Similarity	NPC281702
0.8454	Intermediate Similarity	NPC204450
0.8454	Intermediate Similarity	NPC195290
0.8444	Intermediate Similarity	NPC68160
0.8444	Intermediate Similarity	NPC102683
0.8444	Intermediate Similarity	NPC98442
0.8444	Intermediate Similarity	NPC475740
0.8444	Intermediate Similarity	NPC130577
0.8444	Intermediate Similarity	NPC138756
0.8444	Intermediate Similarity	NPC33768
0.8444	Intermediate Similarity	NPC293564
0.8444	Intermediate Similarity	NPC171203
0.8444	Intermediate Similarity	NPC242468
0.8444	Intermediate Similarity	NPC477926
0.8444	Intermediate Similarity	NPC71507
0.8444	Intermediate Similarity	NPC142415
0.8444	Intermediate Similarity	NPC307426
0.8444	Intermediate Similarity	NPC88716
0.8444	Intermediate Similarity	NPC51700
0.8444	Intermediate Similarity	NPC18064
0.8438	Intermediate Similarity	NPC476274
0.8438	Intermediate Similarity	NPC327431
0.8438	Intermediate Similarity	NPC307954

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 NPC297265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1410
0.2-0.3	3927
0.3-0.4	2478
0.4-0.5	702
0.5-0.6	176
0.6-0.7	167
0.7-0.8	140
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD6399	Phase 3
0.8539	High Similarity	NPD3618	Phase 1
0.8523	High Similarity	NPD4786	Approved
0.8478	Intermediate Similarity	NPD7515	Phase 2
0.8462	Intermediate Similarity	NPD5328	Approved
0.8421	Intermediate Similarity	NPD7902	Approved
0.8317	Intermediate Similarity	NPD6372	Approved
0.8317	Intermediate Similarity	NPD6373	Approved
0.8316	Intermediate Similarity	NPD4697	Phase 3
0.8298	Intermediate Similarity	NPD7748	Approved
0.8295	Intermediate Similarity	NPD3667	Approved
0.828	Intermediate Similarity	NPD8035	Phase 2
0.828	Intermediate Similarity	NPD8034	Phase 2
0.828	Intermediate Similarity	NPD6079	Approved
0.8222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD5739	Approved
0.82	Intermediate Similarity	NPD6675	Approved
0.82	Intermediate Similarity	NPD6402	Approved
0.82	Intermediate Similarity	NPD7128	Approved
0.8155	Intermediate Similarity	NPD6649	Approved
0.8155	Intermediate Similarity	NPD6650	Approved
0.8105	Intermediate Similarity	NPD7900	Approved
0.8105	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD6083	Phase 2
0.8041	Intermediate Similarity	NPD6084	Phase 2
0.8039	Intermediate Similarity	NPD7320	Approved
0.8039	Intermediate Similarity	NPD6899	Approved
0.8039	Intermediate Similarity	NPD6881	Approved
0.8021	Intermediate Similarity	NPD5695	Phase 3
0.8	Intermediate Similarity	NPD4202	Approved
0.7957	Intermediate Similarity	NPD6672	Approved
0.7957	Intermediate Similarity	NPD5737	Approved
0.7941	Intermediate Similarity	NPD5701	Approved
0.7941	Intermediate Similarity	NPD5697	Approved
0.7938	Intermediate Similarity	NPD5221	Approved
0.7938	Intermediate Similarity	NPD5222	Approved
0.7938	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6684	Approved
0.7935	Intermediate Similarity	NPD7146	Approved
0.7935	Intermediate Similarity	NPD7521	Approved
0.7935	Intermediate Similarity	NPD7334	Approved
0.7935	Intermediate Similarity	NPD6409	Approved
0.7935	Intermediate Similarity	NPD5330	Approved
0.7935	Intermediate Similarity	NPD5279	Phase 3
0.7912	Intermediate Similarity	NPD3665	Phase 1
0.7912	Intermediate Similarity	NPD3666	Approved
0.7912	Intermediate Similarity	NPD3133	Approved
0.7895	Intermediate Similarity	NPD5281	Approved
0.7895	Intermediate Similarity	NPD5284	Approved
0.7885	Intermediate Similarity	NPD7102	Approved
0.7885	Intermediate Similarity	NPD7290	Approved
0.7885	Intermediate Similarity	NPD6883	Approved
0.7864	Intermediate Similarity	NPD6011	Approved
0.7857	Intermediate Similarity	NPD5173	Approved
0.7857	Intermediate Similarity	NPD4755	Approved
0.7835	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD6617	Approved
0.781	Intermediate Similarity	NPD6869	Approved
0.781	Intermediate Similarity	NPD8130	Phase 1
0.781	Intermediate Similarity	NPD6847	Approved
0.7788	Intermediate Similarity	NPD6013	Approved
0.7788	Intermediate Similarity	NPD6014	Approved
0.7788	Intermediate Similarity	NPD6012	Approved
0.7778	Intermediate Similarity	NPD7638	Approved
0.7778	Intermediate Similarity	NPD5696	Approved
0.7766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6903	Approved
0.7736	Intermediate Similarity	NPD6882	Approved
0.7736	Intermediate Similarity	NPD8297	Approved
0.7717	Intermediate Similarity	NPD3668	Phase 3
0.7708	Intermediate Similarity	NPD6411	Approved
0.77	Intermediate Similarity	NPD5286	Approved
0.77	Intermediate Similarity	NPD4700	Approved
0.77	Intermediate Similarity	NPD4696	Approved
0.77	Intermediate Similarity	NPD5285	Approved
0.77	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7639	Approved
0.7684	Intermediate Similarity	NPD4753	Phase 2
0.7667	Intermediate Similarity	NPD7525	Registered
0.7624	Intermediate Similarity	NPD5223	Approved
0.7615	Intermediate Similarity	NPD7115	Discovery
0.7614	Intermediate Similarity	NPD6117	Approved
0.7553	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD6098	Approved
0.7549	Intermediate Similarity	NPD4633	Approved
0.7549	Intermediate Similarity	NPD5226	Approved
0.7549	Intermediate Similarity	NPD5224	Approved
0.7549	Intermediate Similarity	NPD5211	Phase 2
0.7549	Intermediate Similarity	NPD5225	Approved
0.7528	Intermediate Similarity	NPD6116	Phase 1
0.7526	Intermediate Similarity	NPD6050	Approved
0.7523	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD4221	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD6101	Approved
0.75	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6673	Approved
0.75	Intermediate Similarity	NPD4223	Phase 3
0.7476	Intermediate Similarity	NPD4754	Approved
0.7476	Intermediate Similarity	NPD5174	Approved
0.7476	Intermediate Similarity	NPD5175	Approved
0.7475	Intermediate Similarity	NPD4629	Approved
0.7475	Intermediate Similarity	NPD5210	Approved
0.7453	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5329	Approved
0.7444	Intermediate Similarity	NPD6115	Approved
0.7444	Intermediate Similarity	NPD6697	Approved
0.7444	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6114	Approved
0.7444	Intermediate Similarity	NPD6118	Approved
0.7423	Intermediate Similarity	NPD5207	Approved
0.7423	Intermediate Similarity	NPD5692	Phase 3
0.7404	Intermediate Similarity	NPD5141	Approved
0.7387	Intermediate Similarity	NPD6335	Approved
0.7386	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6001	Approved
0.7368	Intermediate Similarity	NPD5280	Approved
0.7368	Intermediate Similarity	NPD4694	Approved
0.7368	Intermediate Similarity	NPD5690	Phase 2
0.7364	Intermediate Similarity	NPD6274	Approved
0.7363	Intermediate Similarity	NPD7645	Phase 2
0.7347	Intermediate Similarity	NPD5694	Approved
0.734	Intermediate Similarity	NPD4197	Approved
0.7333	Intermediate Similarity	NPD4767	Approved
0.7333	Intermediate Similarity	NPD4768	Approved
0.7321	Intermediate Similarity	NPD7100	Approved
0.7321	Intermediate Similarity	NPD7101	Approved
0.732	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6317	Approved
0.7297	Intermediate Similarity	NPD6009	Approved
0.7292	Intermediate Similarity	NPD3573	Approved
0.7263	Intermediate Similarity	NPD1694	Approved
0.7234	Intermediate Similarity	NPD4788	Approved
0.7232	Intermediate Similarity	NPD6314	Approved
0.7232	Intermediate Similarity	NPD6313	Approved
0.7222	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5208	Approved
0.7204	Intermediate Similarity	NPD5369	Approved
0.7204	Intermediate Similarity	NPD4139	Approved
0.7204	Intermediate Similarity	NPD4692	Approved
0.7196	Intermediate Similarity	NPD4729	Approved
0.7196	Intermediate Similarity	NPD5168	Approved
0.7196	Intermediate Similarity	NPD4730	Approved
0.7196	Intermediate Similarity	NPD5128	Approved
0.7193	Intermediate Similarity	NPD6909	Approved
0.7193	Intermediate Similarity	NPD6908	Approved
0.7193	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4688	Approved
0.7188	Intermediate Similarity	NPD4693	Phase 3
0.7188	Intermediate Similarity	NPD4690	Approved
0.7188	Intermediate Similarity	NPD4138	Approved
0.7188	Intermediate Similarity	NPD4689	Approved
0.7188	Intermediate Similarity	NPD5205	Approved
0.7172	Intermediate Similarity	NPD5693	Phase 1
0.7159	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6319	Approved
0.7103	Intermediate Similarity	NPD6412	Phase 2
0.71	Intermediate Similarity	NPD5779	Approved
0.71	Intermediate Similarity	NPD5778	Approved
0.7097	Intermediate Similarity	NPD4695	Discontinued
0.7087	Intermediate Similarity	NPD4225	Approved
0.7069	Intermediate Similarity	NPD7604	Phase 2
0.7065	Intermediate Similarity	NPD3617	Approved
0.7064	Intermediate Similarity	NPD5250	Approved
0.7064	Intermediate Similarity	NPD5249	Phase 3
0.7064	Intermediate Similarity	NPD5251	Approved
0.7064	Intermediate Similarity	NPD4634	Approved
0.7064	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5169	Approved
0.7064	Intermediate Similarity	NPD5247	Approved
0.7064	Intermediate Similarity	NPD5248	Approved
0.7064	Intermediate Similarity	NPD5135	Approved
0.7053	Intermediate Similarity	NPD5362	Discontinued
0.7048	Intermediate Similarity	NPD7632	Discontinued
0.7043	Intermediate Similarity	NPD5983	Phase 2
0.701	Intermediate Similarity	NPD5786	Approved
0.7009	Intermediate Similarity	NPD7492	Approved
0.7	Intermediate Similarity	NPD5215	Approved
0.7	Intermediate Similarity	NPD5217	Approved
0.7	Intermediate Similarity	NPD5216	Approved
0.7	Intermediate Similarity	NPD5733	Approved
0.7	Intermediate Similarity	NPD5127	Approved
0.697	Remote Similarity	NPD6051	Approved
0.6961	Remote Similarity	NPD5654	Approved
0.6957	Remote Similarity	NPD6054	Approved
0.6957	Remote Similarity	NPD6059	Approved
0.6949	Remote Similarity	NPD6336	Discontinued
0.6949	Remote Similarity	NPD6616	Approved
0.6947	Remote Similarity	NPD4269	Approved
0.6947	Remote Similarity	NPD6435	Approved
0.6947	Remote Similarity	NPD4270	Approved
0.6947	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3699	Clinical (unspecified phase)

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