NPASS Compound

Structure

NPC313115 OpenBabel07101718292D 24 26 0 0 1 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -1.3660 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 6 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 6 0 0 0 15 18 1 6 0 0 0 15 22 1 0 0 0 0 16 19 1 6 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 18 4 1 6 0 0 0 19 5 1 1 0 0 0 19 24 1 0 0 0 0 20 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.08
Volume:	382.318
LogP:	5.158
LogD:	3.633
LogS:	-4.464
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.383
Synthetic Accessibility Score:	5.717
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.719
MDCK Permeability:	2.087467146338895e-05
Pgp-inhibitor:	0.41
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.195
30% Bioavailability (F30%):	0.263

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.755
Plasma Protein Binding (PPB):	71.71984100341797%
Volume Distribution (VD):	1.513
Pgp-substrate:	23.011104583740234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.137
CYP1A2-substrate:	0.381
CYP2C19-inhibitor:	0.427
CYP2C19-substrate:	0.807
CYP2C9-inhibitor:	0.791
CYP2C9-substrate:	0.213
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.679
CYP3A4-substrate:	0.687

ADMET: Excretion

Clearance (CL):	8.967
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.487
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.155
Rat Oral Acute Toxicity:	0.728
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.364
Carcinogencity:	0.892
Eye Corrosion:	0.787
Eye Irritation:	0.198
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC313115

Natural Product ID:	NPC313115
*Common Name:**	10-Hydroxykahukuene
IUPAC Name:	(1S,2R,3'S,4S,4aS,7S,8aS)-3',4-dibromo-1,2',2',4a-tetramethyl-6'-methylidenespiro[3,4,5,6,8,8a-hexahydro-2H-naphthalene-7,1'-cyclohexane]-1,2-diol
Synonyms:	10-Hydroxykahukuene
Standard InCHIKey:	NMTHADGRZFKZFY-XLXYOEISSA-N
Standard InCHI:	InChI=1S/C20H32Br2O2/c1-12-6-7-14(21)17(2,3)20(12)9-8-18(4)13(11-20)19(5,24)16(23)10-15(18)22/h13-16,23-24H,1,6-11H2,2-5H3/t13-,14-,15-,16+,18-,19-,20-/m0/s1
SMILES:	O[C@@H]1C[C@H](Br)[C@@]2([C@@H]([C@]1(C)O)C[C@@]1(CC2)C(=C)CC[C@@H](C1(C)C)Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL398721
PubChem CID:	24763405
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002517] Chamigranes

*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
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18076141]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	6.5	mm	PMID[490611]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	6.5	mm	PMID[490611]

☑ 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 NPC313115 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	249
0.1-0.2	2903
0.2-0.3	12670
0.3-0.4	14477
0.4-0.5	5807
0.5-0.6	5008
0.6-0.7	1389
0.7-0.8	183
0.8-0.85	6
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9059	High Similarity	NPC239453
0.9059	High Similarity	NPC224552
0.8764	High Similarity	NPC299714
0.8764	High Similarity	NPC257510
0.8462	Intermediate Similarity	NPC156912
0.8391	Intermediate Similarity	NPC174273
0.8375	Intermediate Similarity	NPC237510
0.8375	Intermediate Similarity	NPC475793
0.837	Intermediate Similarity	NPC34732
0.837	Intermediate Similarity	NPC92231
0.8295	Intermediate Similarity	NPC188896
0.809	Intermediate Similarity	NPC131453
0.7975	Intermediate Similarity	NPC244790
0.7952	Intermediate Similarity	NPC91573
0.7882	Intermediate Similarity	NPC129501
0.7831	Intermediate Similarity	NPC476605
0.7765	Intermediate Similarity	NPC102708
0.7738	Intermediate Similarity	NPC470766
0.7677	Intermediate Similarity	NPC133921
0.7654	Intermediate Similarity	NPC210323
0.7619	Intermediate Similarity	NPC3403
0.759	Intermediate Similarity	NPC211009
0.759	Intermediate Similarity	NPC95165
0.759	Intermediate Similarity	NPC476609
0.7586	Intermediate Similarity	NPC13554
0.7561	Intermediate Similarity	NPC45296
0.7531	Intermediate Similarity	NPC2648
0.7529	Intermediate Similarity	NPC476606
0.7528	Intermediate Similarity	NPC85095
0.7528	Intermediate Similarity	NPC207013
0.7528	Intermediate Similarity	NPC211135
0.7528	Intermediate Similarity	NPC216420
0.75	Intermediate Similarity	NPC472503
0.75	Intermediate Similarity	NPC308440
0.747	Intermediate Similarity	NPC111234
0.747	Intermediate Similarity	NPC475077
0.747	Intermediate Similarity	NPC167706
0.747	Intermediate Similarity	NPC301226
0.7468	Intermediate Similarity	NPC101128
0.7442	Intermediate Similarity	NPC470711
0.7442	Intermediate Similarity	NPC470758
0.7416	Intermediate Similarity	NPC477599
0.7416	Intermediate Similarity	NPC47763
0.7412	Intermediate Similarity	NPC212879
0.7412	Intermediate Similarity	NPC477923
0.7412	Intermediate Similarity	NPC240235
0.7412	Intermediate Similarity	NPC144075
0.7412	Intermediate Similarity	NPC70982
0.7412	Intermediate Similarity	NPC178383
0.7412	Intermediate Similarity	NPC185536
0.7412	Intermediate Similarity	NPC104387
0.7412	Intermediate Similarity	NPC230704
0.7412	Intermediate Similarity	NPC66566
0.7412	Intermediate Similarity	NPC231256
0.7407	Intermediate Similarity	NPC185874
0.7407	Intermediate Similarity	NPC269077
0.7407	Intermediate Similarity	NPC253303
0.7407	Intermediate Similarity	NPC139207
0.7386	Intermediate Similarity	NPC236112
0.7356	Intermediate Similarity	NPC301707
0.7356	Intermediate Similarity	NPC31828
0.7356	Intermediate Similarity	NPC472501
0.7356	Intermediate Similarity	NPC472342
0.7356	Intermediate Similarity	NPC42853
0.7356	Intermediate Similarity	NPC285761
0.7333	Intermediate Similarity	NPC159168
0.7333	Intermediate Similarity	NPC253402
0.7326	Intermediate Similarity	NPC278091
0.7326	Intermediate Similarity	NPC86305
0.7326	Intermediate Similarity	NPC93662
0.7326	Intermediate Similarity	NPC78067
0.7326	Intermediate Similarity	NPC470749
0.7326	Intermediate Similarity	NPC14112
0.7312	Intermediate Similarity	NPC475817
0.7303	Intermediate Similarity	NPC474531
0.7294	Intermediate Similarity	NPC25511
0.7294	Intermediate Similarity	NPC62657
0.7294	Intermediate Similarity	NPC254509
0.7294	Intermediate Similarity	NPC145552
0.7294	Intermediate Similarity	NPC196358
0.7294	Intermediate Similarity	NPC5046
0.7294	Intermediate Similarity	NPC192638
0.7294	Intermediate Similarity	NPC476736
0.7294	Intermediate Similarity	NPC49168
0.7294	Intermediate Similarity	NPC100334
0.7283	Intermediate Similarity	NPC475276
0.7283	Intermediate Similarity	NPC121981
0.7273	Intermediate Similarity	NPC49627
0.7273	Intermediate Similarity	NPC49599
0.7273	Intermediate Similarity	NPC273410
0.7273	Intermediate Similarity	NPC329871
0.7273	Intermediate Similarity	NPC476610
0.7273	Intermediate Similarity	NPC291379
0.7273	Intermediate Similarity	NPC83436
0.7273	Intermediate Similarity	NPC80530
0.7253	Intermediate Similarity	NPC238992
0.7253	Intermediate Similarity	NPC255882
0.725	Intermediate Similarity	NPC144650
0.7241	Intermediate Similarity	NPC157996
0.7241	Intermediate Similarity	NPC40394
0.7241	Intermediate Similarity	NPC130136
0.7241	Intermediate Similarity	NPC331618
0.7241	Intermediate Similarity	NPC212241
0.7241	Intermediate Similarity	NPC260301
0.7241	Intermediate Similarity	NPC202540
0.7241	Intermediate Similarity	NPC307336
0.7241	Intermediate Similarity	NPC248830
0.7241	Intermediate Similarity	NPC101475
0.7241	Intermediate Similarity	NPC477924
0.7241	Intermediate Similarity	NPC472805
0.7241	Intermediate Similarity	NPC119355
0.7241	Intermediate Similarity	NPC90979
0.7241	Intermediate Similarity	NPC257191
0.7241	Intermediate Similarity	NPC138502
0.7241	Intermediate Similarity	NPC34177
0.7229	Intermediate Similarity	NPC9942
0.7229	Intermediate Similarity	NPC476604
0.7222	Intermediate Similarity	NPC30166
0.7209	Intermediate Similarity	NPC474946
0.7209	Intermediate Similarity	NPC200243
0.7209	Intermediate Similarity	NPC35397
0.7204	Intermediate Similarity	NPC477600
0.7191	Intermediate Similarity	NPC322313
0.7191	Intermediate Similarity	NPC236237
0.7191	Intermediate Similarity	NPC102253
0.7191	Intermediate Similarity	NPC287749
0.7176	Intermediate Similarity	NPC195489
0.7176	Intermediate Similarity	NPC182717
0.716	Intermediate Similarity	NPC11555
0.716	Intermediate Similarity	NPC282619
0.716	Intermediate Similarity	NPC172613
0.716	Intermediate Similarity	NPC260116
0.716	Intermediate Similarity	NPC208198
0.716	Intermediate Similarity	NPC60837
0.716	Intermediate Similarity	NPC258595
0.716	Intermediate Similarity	NPC2728
0.7159	Intermediate Similarity	NPC158662
0.7159	Intermediate Similarity	NPC6978
0.7159	Intermediate Similarity	NPC477817
0.7159	Intermediate Similarity	NPC300499
0.7159	Intermediate Similarity	NPC99168
0.7159	Intermediate Similarity	NPC470396
0.7159	Intermediate Similarity	NPC477819
0.7159	Intermediate Similarity	NPC474989
0.7159	Intermediate Similarity	NPC230295
0.7159	Intermediate Similarity	NPC244385
0.7159	Intermediate Similarity	NPC22955
0.7159	Intermediate Similarity	NPC167037
0.7159	Intermediate Similarity	NPC196753
0.7159	Intermediate Similarity	NPC253807
0.7159	Intermediate Similarity	NPC472500
0.7159	Intermediate Similarity	NPC472499
0.7159	Intermediate Similarity	NPC98386
0.7159	Intermediate Similarity	NPC138621
0.7143	Intermediate Similarity	NPC97491
0.7143	Intermediate Similarity	NPC273356
0.7128	Intermediate Similarity	NPC473436
0.7126	Intermediate Similarity	NPC30590
0.7126	Intermediate Similarity	NPC120098
0.7126	Intermediate Similarity	NPC38141
0.7126	Intermediate Similarity	NPC265328
0.7126	Intermediate Similarity	NPC27765
0.7126	Intermediate Similarity	NPC30575
0.7126	Intermediate Similarity	NPC290598
0.7126	Intermediate Similarity	NPC63958
0.7126	Intermediate Similarity	NPC122418
0.7126	Intermediate Similarity	NPC274079
0.7126	Intermediate Similarity	NPC477925
0.7126	Intermediate Similarity	NPC476607
0.7126	Intermediate Similarity	NPC237460
0.7111	Intermediate Similarity	NPC311891
0.7108	Intermediate Similarity	NPC245795
0.7108	Intermediate Similarity	NPC276616
0.7108	Intermediate Similarity	NPC475893
0.7108	Intermediate Similarity	NPC94192
0.7097	Intermediate Similarity	NPC94462
0.7097	Intermediate Similarity	NPC71520
0.7097	Intermediate Similarity	NPC237344
0.7097	Intermediate Similarity	NPC269058
0.7093	Intermediate Similarity	NPC476366
0.7093	Intermediate Similarity	NPC201048
0.7093	Intermediate Similarity	NPC91858
0.7093	Intermediate Similarity	NPC477138
0.7093	Intermediate Similarity	NPC243342
0.7079	Intermediate Similarity	NPC472463
0.7079	Intermediate Similarity	NPC24504
0.7079	Intermediate Similarity	NPC476316
0.7079	Intermediate Similarity	NPC80297
0.7079	Intermediate Similarity	NPC116119
0.7079	Intermediate Similarity	NPC475727
0.7079	Intermediate Similarity	NPC476603
0.7079	Intermediate Similarity	NPC53744
0.7079	Intermediate Similarity	NPC472742
0.7079	Intermediate Similarity	NPC328714
0.7073	Intermediate Similarity	NPC473929
0.7059	Intermediate Similarity	NPC242992
0.7053	Intermediate Similarity	NPC329643
0.7045	Intermediate Similarity	NPC471798
0.7037	Intermediate Similarity	NPC68656
0.7033	Intermediate Similarity	NPC218616

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 NPC313115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	3276
0.2-0.3	3945
0.3-0.4	1215
0.4-0.5	220
0.5-0.6	214
0.6-0.7	18
0.7-0.8	1
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
0.7191	Intermediate Similarity	NPD7525	Registered
0.7079	Intermediate Similarity	NPD7645	Phase 2
0.6824	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6942	Approved
0.6629	Remote Similarity	NPD7339	Approved
0.6556	Remote Similarity	NPD6933	Approved
0.6556	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3671	Phase 1
0.6333	Remote Similarity	NPD6924	Approved
0.6333	Remote Similarity	NPD6926	Approved
0.625	Remote Similarity	NPD4788	Approved
0.6238	Remote Similarity	NPD7515	Phase 2
0.6224	Remote Similarity	NPD3618	Phase 1
0.62	Remote Similarity	NPD5328	Approved
0.6186	Remote Similarity	NPD4786	Approved
0.618	Remote Similarity	NPD4787	Phase 1
0.6168	Remote Similarity	NPD7632	Discontinued
0.6146	Remote Similarity	NPD3667	Approved
0.6111	Remote Similarity	NPD4243	Approved
0.6105	Remote Similarity	NPD7509	Discontinued
0.6105	Remote Similarity	NPD4748	Discontinued
0.6078	Remote Similarity	NPD8035	Phase 2
0.6078	Remote Similarity	NPD6079	Approved
0.6078	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7524	Approved
0.5978	Remote Similarity	NPD4784	Approved
0.5978	Remote Similarity	NPD4785	Approved
0.5962	Remote Similarity	NPD7748	Approved
0.5938	Remote Similarity	NPD6931	Approved
0.5938	Remote Similarity	NPD6930	Phase 2
0.5934	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7152	Approved
0.5934	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7150	Approved
0.5934	Remote Similarity	NPD7151	Approved
0.5914	Remote Similarity	NPD8264	Approved
0.5889	Remote Similarity	NPD6922	Approved
0.5889	Remote Similarity	NPD6923	Approved
0.5889	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7638	Approved
0.5859	Remote Similarity	NPD3665	Phase 1
0.5859	Remote Similarity	NPD3666	Approved
0.5859	Remote Similarity	NPD3133	Approved
0.5851	Remote Similarity	NPD6117	Approved
0.5833	Remote Similarity	NPD7639	Approved
0.5833	Remote Similarity	NPD6929	Approved
0.5833	Remote Similarity	NPD7640	Approved
0.5824	Remote Similarity	NPD7144	Approved
0.5824	Remote Similarity	NPD7143	Approved
0.5806	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD4755	Approved
0.5794	Remote Similarity	NPD7902	Approved
0.5789	Remote Similarity	NPD6932	Approved
0.5789	Remote Similarity	NPD6116	Phase 1
0.578	Remote Similarity	NPD4159	Approved
0.5758	Remote Similarity	NPD6695	Phase 3
0.5745	Remote Similarity	NPD3703	Phase 2
0.5745	Remote Similarity	NPD5275	Approved
0.5745	Remote Similarity	NPD4190	Phase 3
0.5729	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6114	Approved
0.5729	Remote Similarity	NPD6697	Approved
0.5729	Remote Similarity	NPD6115	Approved
0.5729	Remote Similarity	NPD6118	Approved
0.5701	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5222	Approved
0.5701	Remote Similarity	NPD4697	Phase 3
0.5701	Remote Similarity	NPD5221	Approved
0.57	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4700	Approved
0.5688	Remote Similarity	NPD5286	Approved
0.5688	Remote Similarity	NPD5285	Approved
0.5688	Remote Similarity	NPD4696	Approved
0.5682	Remote Similarity	NPD371	Approved
0.5678	Remote Similarity	NPD6274	Approved
0.567	Remote Similarity	NPD6683	Phase 2
0.567	Remote Similarity	NPD4195	Approved
0.5652	Remote Similarity	NPD4244	Approved
0.5652	Remote Similarity	NPD4245	Approved
0.5648	Remote Similarity	NPD5173	Approved
0.5644	Remote Similarity	NPD6893	Approved
0.5636	Remote Similarity	NPD5223	Approved
0.5625	Remote Similarity	NPD6925	Approved
0.5625	Remote Similarity	NPD5776	Phase 2
0.5614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD7332	Phase 2
0.5612	Remote Similarity	NPD7514	Phase 3
0.5604	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD5360	Phase 3

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