NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.14
Volume:	278.402
LogP:	3.378
LogD:	3.489
LogS:	-3.294
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	4.802
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.609
MDCK Permeability:	2.190745362895541e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.358
Plasma Protein Binding (PPB):	89.85034942626953%
Volume Distribution (VD):	0.968
Pgp-substrate:	17.76858139038086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.385
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.154
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.302
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	6.357
Half-life (T1/2):	0.414

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.947
Drug-inuced Liver Injury (DILI):	0.138
AMES Toxicity:	0.734
Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.499
Carcinogencity:	0.91
Eye Corrosion:	0.121
Eye Irritation:	0.109
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC153699

Natural Product ID:	NPC153699
*Common Name:**	(Z)-2-((4Ar,6R,7S,8As)-6-Chloro-7-Hydroxy-5,5,8A-Trimethyloctahydronaphthalen-2(1H)-Ylidene)Acetaldehyde
IUPAC Name:	(2Z)-2-[(4aR,6R,7S,8aS)-6-chloro-7-hydroxy-5,5,8a-trimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ylidene]acetaldehyde
Synonyms:
Standard InCHIKey:	HWPNRSYBULQAQB-QLAKETFOSA-N
Standard InCHI:	InChI=1S/C15H23ClO2/c1-14(2)12-5-4-10(6-7-17)8-15(12,3)9-11(18)13(14)16/h6-7,11-13,18H,4-5,8-9H2,1-3H3/b10-6-/t11-,12-,13-,15-/m0/s1
SMILES:	O=C/C=C1/CC[C@@H]2[C@](C1)(C)C[C@@H]([C@@H](C2(C)C)Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447564
PubChem CID:	9881909
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0003131] Alpha,beta-unsaturated carbonyl compounds [CHEMONTID:0002433] Alpha,beta-unsaturated aldehydes [CHEMONTID:0002436] Enals

*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
NPO12253	Stylotella aurantium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11170682]
NPO12253	Stylotella aurantium	n.a.	n.a.	n.a.	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.1	ug.mL-1	PMID[479815]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[479815]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[479815]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[479815]

☑ 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 NPC153699 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	177
0.1-0.2	1530
0.2-0.3	8011
0.3-0.4	17896
0.4-0.5	8185
0.5-0.6	5410
0.6-0.7	1419
0.7-0.8	65
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC76164
0.8193	Intermediate Similarity	NPC470428
0.8095	Intermediate Similarity	NPC476949
0.8	Intermediate Similarity	NPC470429
0.7412	Intermediate Similarity	NPC78527
0.7312	Intermediate Similarity	NPC89747
0.7303	Intermediate Similarity	NPC281880
0.7303	Intermediate Similarity	NPC471514
0.7253	Intermediate Similarity	NPC79945
0.7241	Intermediate Similarity	NPC250621
0.7234	Intermediate Similarity	NPC206060
0.7234	Intermediate Similarity	NPC291665
0.7222	Intermediate Similarity	NPC159148
0.7176	Intermediate Similarity	NPC167706
0.7174	Intermediate Similarity	NPC470812
0.7172	Intermediate Similarity	NPC218902
0.7172	Intermediate Similarity	NPC125771
0.7159	Intermediate Similarity	NPC203403
0.7128	Intermediate Similarity	NPC475772
0.7093	Intermediate Similarity	NPC68443
0.7079	Intermediate Similarity	NPC59436
0.7079	Intermediate Similarity	NPC80088
0.7079	Intermediate Similarity	NPC253561
0.7059	Intermediate Similarity	NPC92801
0.7053	Intermediate Similarity	NPC474925
0.7053	Intermediate Similarity	NPC473229
0.7033	Intermediate Similarity	NPC6434
0.7033	Intermediate Similarity	NPC90055
0.703	Intermediate Similarity	NPC269713
0.7021	Intermediate Similarity	NPC179591
0.7011	Intermediate Similarity	NPC306727
0.7011	Intermediate Similarity	NPC477138
0.7011	Intermediate Similarity	NPC91858
0.7011	Intermediate Similarity	NPC243342
0.7011	Intermediate Similarity	NPC22134
0.7	Intermediate Similarity	NPC283789
0.7	Intermediate Similarity	NPC308038
0.6989	Remote Similarity	NPC33913
0.6989	Remote Similarity	NPC472265
0.6981	Remote Similarity	NPC322912
0.6979	Remote Similarity	NPC472983
0.6977	Remote Similarity	NPC242001
0.6977	Remote Similarity	NPC164022
0.6966	Remote Similarity	NPC149550
0.6966	Remote Similarity	NPC85105
0.6966	Remote Similarity	NPC197659
0.6957	Remote Similarity	NPC93590
0.6957	Remote Similarity	NPC2524
0.6952	Remote Similarity	NPC319438
0.6951	Remote Similarity	NPC144650
0.6932	Remote Similarity	NPC291503
0.6932	Remote Similarity	NPC477923
0.6932	Remote Similarity	NPC66566
0.6915	Remote Similarity	NPC22133
0.6915	Remote Similarity	NPC470574
0.6915	Remote Similarity	NPC109528
0.6907	Remote Similarity	NPC191684
0.6897	Remote Similarity	NPC471799
0.6897	Remote Similarity	NPC182717
0.6889	Remote Similarity	NPC62336
0.6882	Remote Similarity	NPC307258
0.6882	Remote Similarity	NPC64600
0.6875	Remote Similarity	NPC104560
0.6875	Remote Similarity	NPC158778
0.686	Remote Similarity	NPC145498
0.6854	Remote Similarity	NPC263582
0.6854	Remote Similarity	NPC470525
0.6854	Remote Similarity	NPC167873
0.6854	Remote Similarity	NPC1973
0.6854	Remote Similarity	NPC477925
0.6854	Remote Similarity	NPC274079
0.6854	Remote Similarity	NPC253190
0.6848	Remote Similarity	NPC170303
0.6848	Remote Similarity	NPC142163
0.6848	Remote Similarity	NPC119229
0.6842	Remote Similarity	NPC472986
0.6842	Remote Similarity	NPC131813
0.6842	Remote Similarity	NPC477579
0.6842	Remote Similarity	NPC475069
0.6842	Remote Similarity	NPC235341
0.6842	Remote Similarity	NPC175145
0.6842	Remote Similarity	NPC95594
0.6842	Remote Similarity	NPC472985
0.6824	Remote Similarity	NPC208999
0.6824	Remote Similarity	NPC471238
0.6824	Remote Similarity	NPC96484
0.6818	Remote Similarity	NPC471797
0.6818	Remote Similarity	NPC201048
0.6818	Remote Similarity	NPC476366
0.6818	Remote Similarity	NPC100334
0.6813	Remote Similarity	NPC100906
0.6813	Remote Similarity	NPC152061
0.6813	Remote Similarity	NPC170394
0.6804	Remote Similarity	NPC50488
0.6804	Remote Similarity	NPC262858
0.6804	Remote Similarity	NPC474396
0.6804	Remote Similarity	NPC472973
0.6804	Remote Similarity	NPC472240
0.6804	Remote Similarity	NPC119416
0.6792	Remote Similarity	NPC216636
0.6782	Remote Similarity	NPC477792
0.6778	Remote Similarity	NPC219809
0.6778	Remote Similarity	NPC283619
0.6778	Remote Similarity	NPC90979
0.6778	Remote Similarity	NPC157996
0.6778	Remote Similarity	NPC471798
0.6778	Remote Similarity	NPC34177
0.6778	Remote Similarity	NPC40394
0.6778	Remote Similarity	NPC477924
0.6778	Remote Similarity	NPC472805
0.6778	Remote Similarity	NPC101475
0.6778	Remote Similarity	NPC470758
0.6778	Remote Similarity	NPC470711
0.6774	Remote Similarity	NPC48362
0.6771	Remote Similarity	NPC141292
0.6747	Remote Similarity	NPC101128
0.6747	Remote Similarity	NPC225415
0.6747	Remote Similarity	NPC68656
0.6744	Remote Similarity	NPC9942
0.6742	Remote Similarity	NPC257347
0.6742	Remote Similarity	NPC114236
0.6742	Remote Similarity	NPC471723
0.6742	Remote Similarity	NPC141071
0.6739	Remote Similarity	NPC476809
0.6739	Remote Similarity	NPC172013
0.6739	Remote Similarity	NPC472301
0.6739	Remote Similarity	NPC2482
0.6737	Remote Similarity	NPC280203
0.6735	Remote Similarity	NPC310479
0.6735	Remote Similarity	NPC182136
0.6735	Remote Similarity	NPC126993
0.6735	Remote Similarity	NPC85173
0.6735	Remote Similarity	NPC253186
0.6733	Remote Similarity	NPC61369
0.6733	Remote Similarity	NPC5532
0.6733	Remote Similarity	NPC469545
0.6706	Remote Similarity	NPC185874
0.6706	Remote Similarity	NPC68703
0.6706	Remote Similarity	NPC69649
0.6706	Remote Similarity	NPC253303
0.6706	Remote Similarity	NPC269077
0.6706	Remote Similarity	NPC139207
0.6703	Remote Similarity	NPC285761
0.6703	Remote Similarity	NPC22955
0.6703	Remote Similarity	NPC167037
0.6703	Remote Similarity	NPC476314
0.6703	Remote Similarity	NPC196753
0.6703	Remote Similarity	NPC99168
0.6703	Remote Similarity	NPC230295
0.6703	Remote Similarity	NPC6978
0.6703	Remote Similarity	NPC474989
0.6703	Remote Similarity	NPC470396
0.6703	Remote Similarity	NPC158662
0.6703	Remote Similarity	NPC178852
0.6703	Remote Similarity	NPC253807
0.6703	Remote Similarity	NPC98386
0.6703	Remote Similarity	NPC300499
0.6703	Remote Similarity	NPC244385
0.6703	Remote Similarity	NPC138621
0.6702	Remote Similarity	NPC312480
0.6702	Remote Similarity	NPC57370
0.6702	Remote Similarity	NPC97491
0.6702	Remote Similarity	NPC476927
0.6702	Remote Similarity	NPC273356
0.6702	Remote Similarity	NPC311070
0.6701	Remote Similarity	NPC310752
0.6701	Remote Similarity	NPC472802
0.6701	Remote Similarity	NPC328539
0.6701	Remote Similarity	NPC292491
0.6701	Remote Similarity	NPC474677
0.6667	Remote Similarity	NPC31564
0.6667	Remote Similarity	NPC470749
0.6667	Remote Similarity	NPC290598
0.6667	Remote Similarity	NPC321381
0.6667	Remote Similarity	NPC472978
0.6667	Remote Similarity	NPC74296
0.6667	Remote Similarity	NPC30590
0.6667	Remote Similarity	NPC106432
0.6667	Remote Similarity	NPC34834
0.6667	Remote Similarity	NPC14151
0.6667	Remote Similarity	NPC158393
0.6667	Remote Similarity	NPC121984
0.6667	Remote Similarity	NPC282619
0.6667	Remote Similarity	NPC11555
0.6667	Remote Similarity	NPC122418
0.6667	Remote Similarity	NPC474778
0.6667	Remote Similarity	NPC208198
0.6667	Remote Similarity	NPC2728
0.6667	Remote Similarity	NPC145879
0.6667	Remote Similarity	NPC27765
0.6667	Remote Similarity	NPC110923
0.6667	Remote Similarity	NPC72845
0.6667	Remote Similarity	NPC6663
0.6667	Remote Similarity	NPC99380
0.6667	Remote Similarity	NPC94755
0.6667	Remote Similarity	NPC265328
0.6667	Remote Similarity	NPC94666
0.6667	Remote Similarity	NPC473217
0.6667	Remote Similarity	NPC321016
0.6667	Remote Similarity	NPC60837

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 NPC153699 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1828
0.2-0.3	4541
0.3-0.4	2019
0.4-0.5	319
0.5-0.6	219
0.6-0.7	68
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7379	Intermediate Similarity	NPD5168	Approved
0.729	Intermediate Similarity	NPD5167	Approved
0.717	Intermediate Similarity	NPD5215	Approved
0.717	Intermediate Similarity	NPD5216	Approved
0.717	Intermediate Similarity	NPD5217	Approved
0.6909	Remote Similarity	NPD6868	Approved
0.6842	Remote Similarity	NPD3618	Phase 1
0.6759	Remote Similarity	NPD5169	Approved
0.6726	Remote Similarity	NPD7100	Approved
0.6726	Remote Similarity	NPD7101	Approved
0.6697	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6079	Approved
0.6633	Remote Similarity	NPD5328	Approved
0.6632	Remote Similarity	NPD3665	Phase 1
0.6632	Remote Similarity	NPD3666	Approved
0.6632	Remote Similarity	NPD3133	Approved
0.663	Remote Similarity	NPD7645	Phase 2
0.6596	Remote Similarity	NPD3667	Approved
0.6569	Remote Similarity	NPD4697	Phase 3
0.6559	Remote Similarity	NPD7525	Registered
0.6556	Remote Similarity	NPD6942	Approved
0.6556	Remote Similarity	NPD7339	Approved
0.65	Remote Similarity	NPD7515	Phase 2
0.6458	Remote Similarity	NPD4786	Approved
0.6452	Remote Similarity	NPD4195	Approved
0.6444	Remote Similarity	NPD6926	Approved
0.6444	Remote Similarity	NPD6924	Approved
0.6436	Remote Similarity	NPD4202	Approved
0.6435	Remote Similarity	NPD4522	Approved
0.6422	Remote Similarity	NPD5128	Approved
0.6408	Remote Similarity	NPD5222	Approved
0.6408	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5221	Approved
0.6387	Remote Similarity	NPD6336	Discontinued
0.6383	Remote Similarity	NPD4695	Discontinued
0.6348	Remote Similarity	NPD6314	Approved
0.6348	Remote Similarity	NPD6313	Approved
0.6348	Remote Similarity	NPD6335	Approved
0.6346	Remote Similarity	NPD5173	Approved
0.6327	Remote Similarity	NPD5279	Phase 3
0.6304	Remote Similarity	NPD6933	Approved
0.6286	Remote Similarity	NPD5290	Discontinued
0.6286	Remote Similarity	NPD4225	Approved
0.6262	Remote Similarity	NPD5091	Approved
0.6226	Remote Similarity	NPD5286	Approved
0.6226	Remote Similarity	NPD5285	Approved
0.6226	Remote Similarity	NPD4696	Approved
0.6222	Remote Similarity	NPD7151	Approved
0.6222	Remote Similarity	NPD7152	Approved
0.6222	Remote Similarity	NPD7150	Approved
0.6214	Remote Similarity	NPD7748	Approved
0.6211	Remote Similarity	NPD7509	Discontinued
0.6196	Remote Similarity	NPD8264	Approved
0.619	Remote Similarity	NPD4755	Approved
0.618	Remote Similarity	NPD6922	Approved
0.618	Remote Similarity	NPD6923	Approved
0.6168	Remote Similarity	NPD5223	Approved
0.6139	Remote Similarity	NPD4753	Phase 2
0.6132	Remote Similarity	NPD7638	Approved
0.6111	Remote Similarity	NPD5224	Approved
0.6111	Remote Similarity	NPD5211	Phase 2
0.6111	Remote Similarity	NPD7143	Approved
0.6111	Remote Similarity	NPD7144	Approved
0.6111	Remote Similarity	NPD5225	Approved
0.6111	Remote Similarity	NPD5226	Approved
0.6111	Remote Similarity	NPD4633	Approved
0.6105	Remote Similarity	NPD6929	Approved
0.6082	Remote Similarity	NPD4223	Phase 3
0.6082	Remote Similarity	NPD4221	Approved
0.6075	Remote Similarity	NPD4700	Approved
0.6075	Remote Similarity	NPD7639	Approved
0.6075	Remote Similarity	NPD7640	Approved
0.6055	Remote Similarity	NPD5175	Approved
0.6055	Remote Similarity	NPD5174	Approved
0.605	Remote Similarity	NPD5983	Phase 2
0.6042	Remote Similarity	NPD6931	Approved
0.6042	Remote Similarity	NPD6930	Phase 2
0.6038	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4629	Approved
0.6	Remote Similarity	NPD5141	Approved
0.5962	Remote Similarity	NPD5133	Approved
0.596	Remote Similarity	NPD3668	Phase 3
0.596	Remote Similarity	NPD4197	Approved
0.5941	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.592	Remote Similarity	NPD5956	Approved
0.5918	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4754	Approved
0.59	Remote Similarity	NPD1696	Phase 3
0.59	Remote Similarity	NPD5329	Approved
0.59	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6925	Approved
0.5895	Remote Similarity	NPD6932	Approved
0.5895	Remote Similarity	NPD5776	Phase 2
0.5893	Remote Similarity	NPD5697	Approved
0.5876	Remote Similarity	NPD4748	Discontinued
0.5876	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4243	Approved
0.5859	Remote Similarity	NPD4788	Approved
0.5859	Remote Similarity	NPD6695	Phase 3
0.5847	Remote Similarity	NPD6009	Approved
0.5842	Remote Similarity	NPD5690	Phase 2
0.5842	Remote Similarity	NPD7334	Approved
0.5842	Remote Similarity	NPD4690	Approved
0.5842	Remote Similarity	NPD4623	Approved
0.5842	Remote Similarity	NPD4688	Approved
0.5842	Remote Similarity	NPD4693	Phase 3
0.5842	Remote Similarity	NPD6684	Approved
0.5842	Remote Similarity	NPD5330	Approved
0.5842	Remote Similarity	NPD7521	Approved
0.5842	Remote Similarity	NPD6409	Approved
0.5842	Remote Similarity	NPD4689	Approved
0.5842	Remote Similarity	NPD4138	Approved
0.5842	Remote Similarity	NPD5205	Approved
0.5842	Remote Similarity	NPD4519	Discontinued
0.5842	Remote Similarity	NPD7146	Approved
0.5841	Remote Similarity	NPD4729	Approved
0.5841	Remote Similarity	NPD6899	Approved
0.5841	Remote Similarity	NPD6881	Approved
0.5841	Remote Similarity	NPD4730	Approved
0.5841	Remote Similarity	NPD6011	Approved
0.5833	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7145	Approved
0.5833	Remote Similarity	NPD3617	Approved
0.581	Remote Similarity	NPD6399	Phase 3
0.5804	Remote Similarity	NPD6675	Approved
0.5804	Remote Similarity	NPD4768	Approved
0.5804	Remote Similarity	NPD7128	Approved
0.5804	Remote Similarity	NPD5739	Approved
0.5804	Remote Similarity	NPD4767	Approved
0.5804	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6013	Approved
0.5789	Remote Similarity	NPD6014	Approved
0.5789	Remote Similarity	NPD6012	Approved
0.5784	Remote Similarity	NPD3573	Approved
0.5773	Remote Similarity	NPD6683	Phase 2
0.576	Remote Similarity	NPD6033	Approved
0.5755	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7900	Approved
0.5752	Remote Similarity	NPD5701	Approved
0.5745	Remote Similarity	NPD4785	Approved
0.5745	Remote Similarity	NPD4784	Approved
0.5743	Remote Similarity	NPD6893	Approved
0.5741	Remote Similarity	NPD6084	Phase 2
0.5741	Remote Similarity	NPD6083	Phase 2
0.5739	Remote Similarity	NPD6883	Approved
0.5739	Remote Similarity	NPD7290	Approved
0.5739	Remote Similarity	NPD5248	Approved
0.5739	Remote Similarity	NPD4634	Approved
0.5739	Remote Similarity	NPD5250	Approved
0.5739	Remote Similarity	NPD5247	Approved
0.5739	Remote Similarity	NPD5135	Approved
0.5739	Remote Similarity	NPD5251	Approved
0.5739	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD7102	Approved
0.5739	Remote Similarity	NPD5249	Phase 3
0.5728	Remote Similarity	NPD6903	Approved
0.5728	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7514	Phase 3
0.5714	Remote Similarity	NPD7332	Phase 2
0.5702	Remote Similarity	NPD7320	Approved
0.569	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD8130	Phase 1
0.569	Remote Similarity	NPD6650	Approved
0.569	Remote Similarity	NPD6847	Approved
0.569	Remote Similarity	NPD6617	Approved
0.569	Remote Similarity	NPD6649	Approved
0.5686	Remote Similarity	NPD4694	Approved
0.5686	Remote Similarity	NPD5280	Approved
0.5684	Remote Similarity	NPD4190	Phase 3
0.5684	Remote Similarity	NPD5275	Approved
0.5657	Remote Similarity	NPD6898	Phase 1
0.5657	Remote Similarity	NPD6902	Approved
0.5652	Remote Similarity	NPD6373	Approved
0.5652	Remote Similarity	NPD6372	Approved
0.5644	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD8297	Approved
0.5641	Remote Similarity	NPD6882	Approved
0.5631	Remote Similarity	NPD7524	Approved
0.5631	Remote Similarity	NPD7750	Discontinued
0.5614	Remote Similarity	NPD6614	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