NPASS Compound

Structure

NPC266570 OpenBabel07101718192D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.5962 -2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5306 -2.7338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6254 -0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4149 0.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6883 -0.1659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1828 3.8046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9344 -0.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 -0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2435 -1.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8168 1.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4149 2.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8168 0.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4149 1.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2920 -0.2305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6828 2.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2216 -1.7827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8853 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6828 1.9386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5489 0.4386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5489 3.4386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8907 -1.0396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5489 1.4386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6828 -0.0614 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6828 2.9386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1828 3.8046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3853 -2.0101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5489 4.4386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 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 19 1 0 0 0 0 3 20 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 8 18 2 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 20 2 0 0 0 0 11 22 2 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 29 1 0 0 0 0 15 28 1 0 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 30 1 0 0 0 0 17 31 1 0 0 0 0 18 22 1 0 0 0 0 19 26 2 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 32 2 0 0 0 0 22 35 1 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 28 1 1 0 0 0 24 29 1 0 0 0 0 25 30 1 6 0 0 0 25 33 1 0 0 0 0 26 29 1 0 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 28 4 1 6 0 0 0 29 5 1 1 0 0 0 30 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.29
Volume:	518.706
LogP:	3.79
LogD:	3.705
LogS:	-4.653
# Rotatable Bonds:	4
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	4.825
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.806
MDCK Permeability:	2.3386803150060587e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.925
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.379

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	90.55028533935547%
Volume Distribution (VD):	1.241
Pgp-substrate:	5.78907585144043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.551
CYP1A2-substrate:	0.748
CYP2C19-inhibitor:	0.416
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.497
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.365
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.925
CYP3A4-substrate:	0.632

ADMET: Excretion

Clearance (CL):	7.857
Half-life (T1/2):	0.124

ADMET: Toxicity

hERG Blockers:	0.648
Human Hepatotoxicity (H-HT):	0.459
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.648
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.824
Carcinogencity:	0.772
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC266570

Natural Product ID:	NPC266570
*Common Name:**	Rhabdastrellin A
IUPAC Name:	6-[(2E,4E,6E)-6-[(3aS,5aR,6S,7S,9aR,9bS)-7-hydroxy-6-(hydroxymethyl)-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-3-ylidene]hepta-2,4-dien-2-yl]-3-methylpyran-2-one
Synonyms:
Standard InCHIKey:	ZZGSZXWZQYCHPP-YFMITETISA-N
Standard InCHI:	InChI=1S/C30H40O5/c1-18(22-11-10-20(3)27(34)35-22)8-7-9-19(2)26-21(32)16-24-28(4)15-13-25(33)30(6,17-31)23(28)12-14-29(24,26)5/h7-11,23-25,31,33H,12-17H2,1-6H3/b9-7+,18-8+,26-19-/t23-,24+,25+,28+,29+,30-/m1/s1
SMILES:	C/C(=CC=CC(=C/1C(=O)C[C@H]2[C@@]3(C)CC[C@@H]([C@](C)(CO)[C@@H]3CC[C@]12C)O)C)/c1ccc(C)c(=O)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490826
PubChem CID:	25137307
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO32624	rhabdastrella aff. distincta	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620246]
NPO32624	rhabdastrella aff. distincta	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18826276]

☑ 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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4.2	ug.mL-1	PMID[455158]

☑ 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 NPC266570 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	315
0.1-0.2	1254
0.2-0.3	2481
0.3-0.4	4820
0.4-0.5	10469
0.5-0.6	9446
0.6-0.7	9744
0.7-0.8	3828
0.8-0.85	246
0.85-0.9	85
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.94	High Similarity	NPC189863
0.9388	High Similarity	NPC194028
0.9388	High Similarity	NPC168319
0.9381	High Similarity	NPC57079
0.9381	High Similarity	NPC108368
0.9293	High Similarity	NPC114540
0.9293	High Similarity	NPC32577
0.9293	High Similarity	NPC155332
0.9038	High Similarity	NPC16270
0.9	High Similarity	NPC115899
0.898	High Similarity	NPC250757
0.898	High Similarity	NPC301534
0.8952	High Similarity	NPC474315
0.89	High Similarity	NPC266955
0.8889	High Similarity	NPC253826
0.8889	High Similarity	NPC2049
0.8889	High Similarity	NPC110937
0.8824	High Similarity	NPC72151
0.8824	High Similarity	NPC329345
0.8824	High Similarity	NPC473283
0.8824	High Similarity	NPC475526
0.8824	High Similarity	NPC112009
0.8812	High Similarity	NPC282524
0.8807	High Similarity	NPC146786
0.8788	High Similarity	NPC16967
0.8788	High Similarity	NPC471153
0.8785	High Similarity	NPC73050
0.8762	High Similarity	NPC475065
0.875	High Similarity	NPC330011
0.875	High Similarity	NPC329048
0.8725	High Similarity	NPC320447
0.8713	High Similarity	NPC201406
0.8713	High Similarity	NPC35751
0.8687	High Similarity	NPC88310
0.8687	High Similarity	NPC180950
0.8673	High Similarity	NPC139692
0.8667	High Similarity	NPC473482
0.8667	High Similarity	NPC475418
0.8667	High Similarity	NPC318363
0.8667	High Similarity	NPC220155
0.866	High Similarity	NPC475965
0.866	High Similarity	NPC474842
0.8654	High Similarity	NPC34768
0.8649	High Similarity	NPC114939
0.8649	High Similarity	NPC41123
0.8649	High Similarity	NPC145074
0.8641	High Similarity	NPC180204
0.8641	High Similarity	NPC171014
0.8614	High Similarity	NPC98868
0.8611	High Similarity	NPC122056
0.8586	High Similarity	NPC191521
0.8586	High Similarity	NPC474690
0.8586	High Similarity	NPC299100
0.8585	High Similarity	NPC75389
0.8585	High Similarity	NPC137911
0.8585	High Similarity	NPC228477
0.8571	High Similarity	NPC179380
0.8571	High Similarity	NPC473284
0.8571	High Similarity	NPC79298
0.8571	High Similarity	NPC43063
0.8532	High Similarity	NPC147912
0.8532	High Similarity	NPC67259
0.8529	High Similarity	NPC474012
0.8529	High Similarity	NPC476299
0.8519	High Similarity	NPC69291
0.8491	Intermediate Similarity	NPC137462
0.8491	Intermediate Similarity	NPC304276
0.8491	Intermediate Similarity	NPC275060
0.8485	Intermediate Similarity	NPC205034
0.8485	Intermediate Similarity	NPC152778
0.8485	Intermediate Similarity	NPC162615
0.8482	Intermediate Similarity	NPC184555
0.8476	Intermediate Similarity	NPC295843
0.8462	Intermediate Similarity	NPC475050
0.8462	Intermediate Similarity	NPC297617
0.8454	Intermediate Similarity	NPC310752
0.8454	Intermediate Similarity	NPC292491
0.8421	Intermediate Similarity	NPC55602
0.8416	Intermediate Similarity	NPC122324
0.8416	Intermediate Similarity	NPC106425
0.8416	Intermediate Similarity	NPC134072
0.8416	Intermediate Similarity	NPC151725
0.8416	Intermediate Similarity	NPC242848
0.8416	Intermediate Similarity	NPC234993
0.84	Intermediate Similarity	NPC471078
0.84	Intermediate Similarity	NPC473280
0.84	Intermediate Similarity	NPC473435
0.84	Intermediate Similarity	NPC473431
0.8396	Intermediate Similarity	NPC91034
0.8396	Intermediate Similarity	NPC475294
0.8396	Intermediate Similarity	NPC302788
0.8384	Intermediate Similarity	NPC473986
0.8384	Intermediate Similarity	NPC474018
0.8378	Intermediate Similarity	NPC20302
0.8378	Intermediate Similarity	NPC140055
0.8378	Intermediate Similarity	NPC470492
0.8378	Intermediate Similarity	NPC286528
0.8378	Intermediate Similarity	NPC167606
0.8367	Intermediate Similarity	NPC174342
0.8367	Intermediate Similarity	NPC474844
0.8351	Intermediate Similarity	NPC163016
0.8351	Intermediate Similarity	NPC141292
0.8351	Intermediate Similarity	NPC75315
0.835	Intermediate Similarity	NPC117685
0.835	Intermediate Similarity	NPC251680
0.8349	Intermediate Similarity	NPC44537
0.8333	Intermediate Similarity	NPC474785
0.8333	Intermediate Similarity	NPC53844
0.8333	Intermediate Similarity	NPC103491
0.8333	Intermediate Similarity	NPC12795
0.8333	Intermediate Similarity	NPC202705
0.8333	Intermediate Similarity	NPC474938
0.8333	Intermediate Similarity	NPC108078
0.8319	Intermediate Similarity	NPC476962
0.8318	Intermediate Similarity	NPC472825
0.8317	Intermediate Similarity	NPC139459
0.8317	Intermediate Similarity	NPC209355
0.8317	Intermediate Similarity	NPC33473
0.8317	Intermediate Similarity	NPC171395
0.8304	Intermediate Similarity	NPC473617
0.8304	Intermediate Similarity	NPC50774
0.8304	Intermediate Similarity	NPC473828
0.8304	Intermediate Similarity	NPC709
0.8302	Intermediate Similarity	NPC478208
0.8302	Intermediate Similarity	NPC478052
0.8286	Intermediate Similarity	NPC476237
0.8286	Intermediate Similarity	NPC476889
0.8283	Intermediate Similarity	NPC161638
0.8283	Intermediate Similarity	NPC310479
0.8273	Intermediate Similarity	NPC171126
0.8269	Intermediate Similarity	NPC471412
0.8269	Intermediate Similarity	NPC118174
0.8269	Intermediate Similarity	NPC476223
0.8269	Intermediate Similarity	NPC476240
0.8269	Intermediate Similarity	NPC224720
0.8265	Intermediate Similarity	NPC104560
0.8261	Intermediate Similarity	NPC6193
0.8252	Intermediate Similarity	NPC478056
0.8252	Intermediate Similarity	NPC278673
0.8252	Intermediate Similarity	NPC316598
0.8252	Intermediate Similarity	NPC103051
0.8252	Intermediate Similarity	NPC92275
0.8235	Intermediate Similarity	NPC190713
0.823	Intermediate Similarity	NPC264954
0.822	Intermediate Similarity	NPC221414
0.8218	Intermediate Similarity	NPC469406
0.8214	Intermediate Similarity	NPC312824
0.8214	Intermediate Similarity	NPC470493
0.8214	Intermediate Similarity	NPC183580
0.8214	Intermediate Similarity	NPC243065
0.8208	Intermediate Similarity	NPC472868
0.82	Intermediate Similarity	NPC72845
0.8198	Intermediate Similarity	NPC475163
0.819	Intermediate Similarity	NPC469606
0.819	Intermediate Similarity	NPC476890
0.819	Intermediate Similarity	NPC476081
0.819	Intermediate Similarity	NPC273005
0.819	Intermediate Similarity	NPC31058
0.819	Intermediate Similarity	NPC40918
0.819	Intermediate Similarity	NPC136289
0.8182	Intermediate Similarity	NPC474704
0.8182	Intermediate Similarity	NPC264634
0.8182	Intermediate Similarity	NPC100267
0.8182	Intermediate Similarity	NPC5509
0.8182	Intermediate Similarity	NPC475921
0.8182	Intermediate Similarity	NPC475524
0.8173	Intermediate Similarity	NPC476303
0.8173	Intermediate Similarity	NPC476274
0.8173	Intermediate Similarity	NPC471413
0.8165	Intermediate Similarity	NPC478209
0.8165	Intermediate Similarity	NPC179642
0.8158	Intermediate Similarity	NPC474370
0.8155	Intermediate Similarity	NPC141401
0.8155	Intermediate Similarity	NPC208094
0.8155	Intermediate Similarity	NPC474343
0.8142	Intermediate Similarity	NPC311554
0.8142	Intermediate Similarity	NPC257457
0.8137	Intermediate Similarity	NPC183012
0.8137	Intermediate Similarity	NPC476174
0.8137	Intermediate Similarity	NPC295347
0.8137	Intermediate Similarity	NPC293052
0.8131	Intermediate Similarity	NPC469607
0.8125	Intermediate Similarity	NPC64318
0.8125	Intermediate Similarity	NPC476963
0.812	Intermediate Similarity	NPC159499
0.8119	Intermediate Similarity	NPC472871
0.8119	Intermediate Similarity	NPC38232
0.8119	Intermediate Similarity	NPC214697
0.8113	Intermediate Similarity	NPC120321
0.8113	Intermediate Similarity	NPC176883
0.8113	Intermediate Similarity	NPC478057
0.8113	Intermediate Similarity	NPC291154
0.8108	Intermediate Similarity	NPC154815
0.8108	Intermediate Similarity	NPC25909
0.8108	Intermediate Similarity	NPC241977
0.81	Intermediate Similarity	NPC280149
0.81	Intermediate Similarity	NPC471896
0.81	Intermediate Similarity	NPC221111
0.81	Intermediate Similarity	NPC78973
0.81	Intermediate Similarity	NPC51486

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 NPC266570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	793
0.2-0.3	1404
0.3-0.4	2421
0.4-0.5	2311
0.5-0.6	1373
0.6-0.7	479
0.7-0.8	90
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8431	Intermediate Similarity	NPD7638	Approved
0.8378	Intermediate Similarity	NPD7115	Discovery
0.835	Intermediate Similarity	NPD7639	Approved
0.835	Intermediate Similarity	NPD7640	Approved
0.8148	Intermediate Similarity	NPD6899	Approved
0.8148	Intermediate Similarity	NPD6881	Approved
0.8056	Intermediate Similarity	NPD5697	Approved
0.802	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD7290	Approved
0.8	Intermediate Similarity	NPD6883	Approved
0.7963	Intermediate Similarity	NPD6402	Approved
0.7963	Intermediate Similarity	NPD7128	Approved
0.7963	Intermediate Similarity	NPD5739	Approved
0.7963	Intermediate Similarity	NPD6675	Approved
0.7928	Intermediate Similarity	NPD6650	Approved
0.7928	Intermediate Similarity	NPD8130	Phase 1
0.7928	Intermediate Similarity	NPD6617	Approved
0.7928	Intermediate Similarity	NPD6649	Approved
0.7928	Intermediate Similarity	NPD6869	Approved
0.7928	Intermediate Similarity	NPD6847	Approved
0.7909	Intermediate Similarity	NPD6014	Approved
0.7909	Intermediate Similarity	NPD6012	Approved
0.7909	Intermediate Similarity	NPD6013	Approved
0.7879	Intermediate Similarity	NPD3618	Phase 1
0.7864	Intermediate Similarity	NPD7748	Approved
0.7857	Intermediate Similarity	NPD8297	Approved
0.7857	Intermediate Similarity	NPD6882	Approved
0.7843	Intermediate Similarity	NPD7515	Phase 2
0.7822	Intermediate Similarity	NPD5328	Approved
0.7818	Intermediate Similarity	NPD7320	Approved
0.7818	Intermediate Similarity	NPD6011	Approved
0.781	Intermediate Similarity	NPD6084	Phase 2
0.781	Intermediate Similarity	NPD6083	Phase 2
0.7767	Intermediate Similarity	NPD6399	Phase 3
0.7748	Intermediate Similarity	NPD6372	Approved
0.7748	Intermediate Similarity	NPD6373	Approved
0.7736	Intermediate Similarity	NPD4225	Approved
0.7727	Intermediate Similarity	NPD5701	Approved
0.7714	Intermediate Similarity	NPD5222	Approved
0.7714	Intermediate Similarity	NPD5221	Approved
0.7714	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD6684	Approved
0.77	Intermediate Similarity	NPD7334	Approved
0.77	Intermediate Similarity	NPD7146	Approved
0.77	Intermediate Similarity	NPD7521	Approved
0.77	Intermediate Similarity	NPD6409	Approved
0.77	Intermediate Similarity	NPD5330	Approved
0.7685	Intermediate Similarity	NPD7632	Discontinued
0.7685	Intermediate Similarity	NPD5211	Phase 2
0.7664	Intermediate Similarity	NPD5285	Approved
0.7664	Intermediate Similarity	NPD5286	Approved
0.7664	Intermediate Similarity	NPD4696	Approved
0.7653	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7902	Approved
0.7642	Intermediate Similarity	NPD5173	Approved
0.7627	Intermediate Similarity	NPD7503	Approved
0.76	Intermediate Similarity	NPD1694	Approved
0.7549	Intermediate Similarity	NPD5737	Approved
0.7549	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6903	Approved
0.7549	Intermediate Similarity	NPD6672	Approved
0.7545	Intermediate Similarity	NPD5141	Approved
0.7523	Intermediate Similarity	NPD5224	Approved
0.7523	Intermediate Similarity	NPD5225	Approved
0.7523	Intermediate Similarity	NPD5226	Approved
0.7523	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.7477	Intermediate Similarity	NPD4755	Approved
0.7475	Intermediate Similarity	NPD3667	Approved
0.7458	Intermediate Similarity	NPD7101	Approved
0.7458	Intermediate Similarity	NPD7100	Approved
0.7456	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5175	Approved
0.7455	Intermediate Similarity	NPD5174	Approved
0.7453	Intermediate Similarity	NPD5695	Phase 3
0.7431	Intermediate Similarity	NPD5223	Approved
0.7429	Intermediate Similarity	NPD4202	Approved
0.7426	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5696	Approved
0.7404	Intermediate Similarity	NPD5785	Approved
0.7391	Intermediate Similarity	NPD6053	Discontinued
0.7383	Intermediate Similarity	NPD4697	Phase 3
0.7373	Intermediate Similarity	NPD6335	Approved
0.7358	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7900	Approved
0.7353	Intermediate Similarity	NPD5279	Phase 3
0.735	Intermediate Similarity	NPD6274	Approved
0.7339	Intermediate Similarity	NPD4700	Approved
0.7333	Intermediate Similarity	NPD5693	Phase 1
0.7333	Intermediate Similarity	NPD8035	Phase 2
0.7333	Intermediate Similarity	NPD5284	Approved
0.7333	Intermediate Similarity	NPD7637	Suspended
0.7333	Intermediate Similarity	NPD6411	Approved
0.7333	Intermediate Similarity	NPD8034	Phase 2
0.7333	Intermediate Similarity	NPD5281	Approved
0.7328	Intermediate Similarity	NPD4632	Approved
0.7308	Intermediate Similarity	NPD4753	Phase 2
0.729	Intermediate Similarity	NPD4629	Approved
0.729	Intermediate Similarity	NPD5210	Approved
0.729	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6317	Approved
0.7282	Intermediate Similarity	NPD3573	Approved
0.7281	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6319	Approved
0.7236	Intermediate Similarity	NPD7507	Approved
0.7227	Intermediate Similarity	NPD6313	Approved
0.7227	Intermediate Similarity	NPD6314	Approved
0.7193	Intermediate Similarity	NPD4729	Approved
0.7193	Intermediate Similarity	NPD4730	Approved
0.7184	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6050	Approved
0.717	Intermediate Similarity	NPD5694	Approved
0.7154	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6904	Approved
0.7143	Intermediate Similarity	NPD6080	Approved
0.7107	Intermediate Similarity	NPD6054	Approved
0.7105	Intermediate Similarity	NPD6412	Phase 2
0.7103	Intermediate Similarity	NPD5778	Approved
0.7103	Intermediate Similarity	NPD5779	Approved
0.7097	Intermediate Similarity	NPD6616	Approved
0.7075	Intermediate Similarity	NPD5692	Phase 3
0.7075	Intermediate Similarity	NPD5207	Approved
0.7073	Intermediate Similarity	NPD7604	Phase 2
0.7071	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5250	Approved
0.7069	Intermediate Similarity	NPD5249	Phase 3
0.7069	Intermediate Similarity	NPD5251	Approved
0.7069	Intermediate Similarity	NPD4634	Approved
0.7069	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5247	Approved
0.7069	Intermediate Similarity	NPD5248	Approved
0.7063	Intermediate Similarity	NPD7319	Approved
0.7059	Intermediate Similarity	NPD7154	Phase 3
0.7059	Intermediate Similarity	NPD4788	Approved
0.7049	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6908	Approved
0.7049	Intermediate Similarity	NPD5983	Phase 2
0.7049	Intermediate Similarity	NPD6909	Approved
0.7043	Intermediate Similarity	NPD5168	Approved
0.7043	Intermediate Similarity	NPD5128	Approved
0.704	Intermediate Similarity	NPD7078	Approved
0.7018	Intermediate Similarity	NPD4767	Approved
0.7018	Intermediate Similarity	NPD4768	Approved
0.7018	Intermediate Similarity	NPD6008	Approved
0.7009	Intermediate Similarity	NPD5215	Approved
0.7009	Intermediate Similarity	NPD5217	Approved
0.7009	Intermediate Similarity	NPD5216	Approved
0.6992	Remote Similarity	NPD6370	Approved
0.6991	Remote Similarity	NPD4754	Approved
0.699	Remote Similarity	NPD3668	Phase 3
0.6984	Remote Similarity	NPD7736	Approved
0.6981	Remote Similarity	NPD6051	Approved
0.6972	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4223	Phase 3
0.6961	Remote Similarity	NPD4221	Approved
0.696	Remote Similarity	NPD6336	Discontinued
0.6953	Remote Similarity	NPD7260	Phase 2
0.6942	Remote Similarity	NPD7328	Approved
0.6942	Remote Similarity	NPD7327	Approved
0.6931	Remote Similarity	NPD7525	Registered
0.6931	Remote Similarity	NPD4695	Discontinued
0.6923	Remote Similarity	NPD5363	Approved
0.6923	Remote Similarity	NPD5135	Approved
0.6923	Remote Similarity	NPD5329	Approved
0.6923	Remote Similarity	NPD5169	Approved
0.6923	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6015	Approved
0.6911	Remote Similarity	NPD6016	Approved
0.69	Remote Similarity	NPD3617	Approved
0.6897	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5208	Approved
0.6885	Remote Similarity	NPD7516	Approved
0.6881	Remote Similarity	NPD6001	Approved
0.6875	Remote Similarity	NPD6404	Discontinued
0.6869	Remote Similarity	NPD6117	Approved
0.6864	Remote Similarity	NPD5127	Approved
0.6857	Remote Similarity	NPD4519	Discontinued
0.6857	Remote Similarity	NPD6098	Approved
0.6857	Remote Similarity	NPD5280	Approved
0.6857	Remote Similarity	NPD4623	Approved
0.6857	Remote Similarity	NPD4694	Approved
0.6857	Remote Similarity	NPD5690	Phase 2
0.6855	Remote Similarity	NPD5988	Approved
0.6837	Remote Similarity	NPD4058	Approved
0.6829	Remote Similarity	NPD8294	Approved
0.6829	Remote Similarity	NPD6059	Approved
0.6829	Remote Similarity	NPD8377	Approved
0.6827	Remote Similarity	NPD4197	Approved
0.681	Remote Similarity	NPD5954	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