NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	385.377
LogP:	5.524
LogD:	3.569
LogS:	-4.104
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.304
Synthetic Accessibility Score:	3.947
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.812
MDCK Permeability:	1.5157542293309234e-05
Pgp-inhibitor:	0.31
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.275

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	99.39209747314453%
Volume Distribution (VD):	4.82
Pgp-substrate:	1.1793090105056763%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.501
CYP2C19-inhibitor:	0.563
CYP2C19-substrate:	0.494
CYP2C9-inhibitor:	0.543
CYP2C9-substrate:	0.867
CYP2D6-inhibitor:	0.502
CYP2D6-substrate:	0.347
CYP3A4-inhibitor:	0.33
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	13.118
Half-life (T1/2):	0.31

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.204
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.554
Skin Sensitization:	0.938
Carcinogencity:	0.139
Eye Corrosion:	0.186
Eye Irritation:	0.922
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC476535

Natural Product ID:	NPC476535
*Common Name:**	3-[(E)-[(2S,8aS)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-ylidene]methyl]-2,5,6-trihydroxybenzaldehyde
IUPAC Name:	3-[(E)-[(2S,8aS)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-ylidene]methyl]-2,5,6-trihydroxybenzaldehyde
Synonyms:
Standard InCHIKey:	VGSQRECMCPQJNS-QGKRBUCPSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-13-6-7-18-21(2,3)8-5-9-22(18,4)16(13)10-14-11-17(24)20(26)15(12-23)19(14)25/h10-13,18,24-26H,5-9H2,1-4H3/b16-10+/t13-,18?,22+/m0/s1
SMILES:	C[C@H]\1CCC2[C@@](/C1=C/C3=CC(=C(C(=C3O)C=O)O)O)(CCCC2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11962162
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001310] Benzenetriols and derivatives [CHEMONTID:0000380] Hydroxyquinols and derivatives

*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
NPO9771	Aka coralliphagum	Species	Niphatidae	Eukaryota	n.a.	San Salvador in the Bahamas (12-26 m depth)	2001-MAR; 2003-JUL	PMID[17309298]
NPO9771	Aka coralliphagum	Species	Niphatidae	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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	Activity	=	0.2	ug/ml	PMID[17309298]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	9	mm	PMID[17309298]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12	mm	PMID[17309298]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	0	mm	PMID[17309298]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IZ	=	15	mm	PMID[17309298]

☑ 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 NPC476535 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	390
0.1-0.2	1425
0.2-0.3	3057
0.3-0.4	7874
0.4-0.5	11116
0.5-0.6	5338
0.6-0.7	8208
0.7-0.8	5150
0.8-0.85	125
0.85-0.9	10
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC476532
0.9586	High Similarity	NPC476533
0.9583	High Similarity	NPC474191
0.8958	High Similarity	NPC92079
0.8926	High Similarity	NPC48949
0.8881	High Similarity	NPC141368
0.8881	High Similarity	NPC206207
0.8828	High Similarity	NPC187843
0.8716	High Similarity	NPC68441
0.8707	High Similarity	NPC238629
0.8707	High Similarity	NPC199936
0.863	High Similarity	NPC471853
0.863	High Similarity	NPC476534
0.8542	High Similarity	NPC475917
0.8533	High Similarity	NPC63918
0.8528	High Similarity	NPC478050
0.8523	High Similarity	NPC244691
0.8514	High Similarity	NPC474961
0.8503	High Similarity	NPC203063
0.8493	Intermediate Similarity	NPC123714
0.8483	Intermediate Similarity	NPC264112
0.8483	Intermediate Similarity	NPC65005
0.8483	Intermediate Similarity	NPC194764
0.8472	Intermediate Similarity	NPC474117
0.8472	Intermediate Similarity	NPC474224
0.8471	Intermediate Similarity	NPC155302
0.8471	Intermediate Similarity	NPC161947
0.8451	Intermediate Similarity	NPC244441
0.8442	Intermediate Similarity	NPC161778
0.8435	Intermediate Similarity	NPC143438
0.8431	Intermediate Similarity	NPC280295
0.8428	Intermediate Similarity	NPC101769
0.8425	Intermediate Similarity	NPC290030
0.8418	Intermediate Similarity	NPC472275
0.8418	Intermediate Similarity	NPC87431
0.8418	Intermediate Similarity	NPC32694
0.84	Intermediate Similarity	NPC10764
0.8392	Intermediate Similarity	NPC85342
0.8392	Intermediate Similarity	NPC291001
0.8389	Intermediate Similarity	NPC135524
0.8389	Intermediate Similarity	NPC248068
0.8387	Intermediate Similarity	NPC273248
0.8378	Intermediate Similarity	NPC169452
0.8378	Intermediate Similarity	NPC181560
0.8375	Intermediate Similarity	NPC473286
0.8365	Intermediate Similarity	NPC470694
0.8356	Intermediate Similarity	NPC191976
0.8355	Intermediate Similarity	NPC10842
0.8354	Intermediate Similarity	NPC84571
0.8354	Intermediate Similarity	NPC45146
0.8354	Intermediate Similarity	NPC235018
0.8354	Intermediate Similarity	NPC297212
0.8344	Intermediate Similarity	NPC75295
0.8333	Intermediate Similarity	NPC134287
0.8333	Intermediate Similarity	NPC68727
0.8333	Intermediate Similarity	NPC130589
0.8323	Intermediate Similarity	NPC470338
0.8323	Intermediate Similarity	NPC113608
0.8323	Intermediate Similarity	NPC470337
0.8323	Intermediate Similarity	NPC268992
0.8323	Intermediate Similarity	NPC51824
0.8322	Intermediate Similarity	NPC62219
0.8322	Intermediate Similarity	NPC305845
0.8322	Intermediate Similarity	NPC204045
0.8322	Intermediate Similarity	NPC472904
0.8313	Intermediate Similarity	NPC220313
0.8313	Intermediate Similarity	NPC472278
0.8313	Intermediate Similarity	NPC329669
0.8313	Intermediate Similarity	NPC473313
0.8313	Intermediate Similarity	NPC476295
0.8312	Intermediate Similarity	NPC470037
0.8311	Intermediate Similarity	NPC162939
0.8311	Intermediate Similarity	NPC190457
0.8311	Intermediate Similarity	NPC242994
0.8311	Intermediate Similarity	NPC472903
0.8311	Intermediate Similarity	NPC138099
0.8302	Intermediate Similarity	NPC311740
0.8301	Intermediate Similarity	NPC471907
0.8299	Intermediate Similarity	NPC471905
0.8299	Intermediate Similarity	NPC147418
0.8291	Intermediate Similarity	NPC46736
0.8291	Intermediate Similarity	NPC185258
0.8291	Intermediate Similarity	NPC172770
0.828	Intermediate Similarity	NPC142339
0.828	Intermediate Similarity	NPC474167
0.828	Intermediate Similarity	NPC470762
0.8278	Intermediate Similarity	NPC471906
0.8276	Intermediate Similarity	NPC111845
0.8276	Intermediate Similarity	NPC267205
0.8269	Intermediate Similarity	NPC93552
0.8269	Intermediate Similarity	NPC107109
0.8269	Intermediate Similarity	NPC477048
0.8269	Intermediate Similarity	NPC477047
0.8267	Intermediate Similarity	NPC291078
0.8267	Intermediate Similarity	NPC73061
0.8267	Intermediate Similarity	NPC193555
0.8258	Intermediate Similarity	NPC35
0.8258	Intermediate Similarity	NPC75377
0.8258	Intermediate Similarity	NPC221249
0.8243	Intermediate Similarity	NPC416
0.8243	Intermediate Similarity	NPC230811
0.8243	Intermediate Similarity	NPC61398
0.8239	Intermediate Similarity	NPC80375
0.8239	Intermediate Similarity	NPC476280
0.8239	Intermediate Similarity	NPC56085
0.8239	Intermediate Similarity	NPC228785
0.8239	Intermediate Similarity	NPC14353
0.8239	Intermediate Similarity	NPC119224
0.8232	Intermediate Similarity	NPC307286
0.8231	Intermediate Similarity	NPC223836
0.8231	Intermediate Similarity	NPC254847
0.8231	Intermediate Similarity	NPC471690
0.8228	Intermediate Similarity	NPC469584
0.8228	Intermediate Similarity	NPC37543
0.8228	Intermediate Similarity	NPC79053
0.8228	Intermediate Similarity	NPC78103
0.8228	Intermediate Similarity	NPC199463
0.8228	Intermediate Similarity	NPC236796
0.8228	Intermediate Similarity	NPC179732
0.8227	Intermediate Similarity	NPC131799
0.8224	Intermediate Similarity	NPC258856
0.8224	Intermediate Similarity	NPC34482
0.8219	Intermediate Similarity	NPC282780
0.8219	Intermediate Similarity	NPC474519
0.8219	Intermediate Similarity	NPC293454
0.8219	Intermediate Similarity	NPC166480
0.8219	Intermediate Similarity	NPC474394
0.8217	Intermediate Similarity	NPC39184
0.8217	Intermediate Similarity	NPC472048
0.8217	Intermediate Similarity	NPC113906
0.8207	Intermediate Similarity	NPC175738
0.8207	Intermediate Similarity	NPC135801
0.8205	Intermediate Similarity	NPC180944
0.8205	Intermediate Similarity	NPC3744
0.8199	Intermediate Similarity	NPC236132
0.8199	Intermediate Similarity	NPC270837
0.8199	Intermediate Similarity	NPC12461
0.8199	Intermediate Similarity	NPC7483
0.8194	Intermediate Similarity	NPC10467
0.8194	Intermediate Similarity	NPC233056
0.8187	Intermediate Similarity	NPC61010
0.8187	Intermediate Similarity	NPC40491
0.8187	Intermediate Similarity	NPC266314
0.8187	Intermediate Similarity	NPC278052
0.8187	Intermediate Similarity	NPC278427
0.8182	Intermediate Similarity	NPC203077
0.8182	Intermediate Similarity	NPC166036
0.8182	Intermediate Similarity	NPC471969
0.8182	Intermediate Similarity	NPC238279
0.8176	Intermediate Similarity	NPC85121
0.8176	Intermediate Similarity	NPC329091
0.8176	Intermediate Similarity	NPC277559
0.8176	Intermediate Similarity	NPC100123
0.8176	Intermediate Similarity	NPC170742
0.8176	Intermediate Similarity	NPC53206
0.8176	Intermediate Similarity	NPC197856
0.8176	Intermediate Similarity	NPC49911
0.8176	Intermediate Similarity	NPC53414
0.8176	Intermediate Similarity	NPC53001
0.817	Intermediate Similarity	NPC470570
0.8169	Intermediate Similarity	NPC49647
0.8169	Intermediate Similarity	NPC136342
0.8169	Intermediate Similarity	NPC227741
0.8169	Intermediate Similarity	NPC295202
0.8165	Intermediate Similarity	NPC77807
0.8165	Intermediate Similarity	NPC5379
0.8165	Intermediate Similarity	NPC14561
0.8163	Intermediate Similarity	NPC153088
0.8163	Intermediate Similarity	NPC278375
0.8163	Intermediate Similarity	NPC14377
0.8163	Intermediate Similarity	NPC290803
0.8163	Intermediate Similarity	NPC129752
0.816	Intermediate Similarity	NPC470374
0.816	Intermediate Similarity	NPC478060
0.816	Intermediate Similarity	NPC478059
0.816	Intermediate Similarity	NPC470377
0.816	Intermediate Similarity	NPC471975
0.816	Intermediate Similarity	NPC107009
0.8158	Intermediate Similarity	NPC193703
0.8158	Intermediate Similarity	NPC21599
0.8158	Intermediate Similarity	NPC48762
0.8153	Intermediate Similarity	NPC89474
0.8153	Intermediate Similarity	NPC250557
0.8153	Intermediate Similarity	NPC124714
0.8151	Intermediate Similarity	NPC314048
0.8151	Intermediate Similarity	NPC138472
0.8148	Intermediate Similarity	NPC25361
0.8148	Intermediate Similarity	NPC326520
0.8146	Intermediate Similarity	NPC137649
0.8141	Intermediate Similarity	NPC70320
0.8141	Intermediate Similarity	NPC19980
0.8141	Intermediate Similarity	NPC227485
0.8141	Intermediate Similarity	NPC45291
0.8138	Intermediate Similarity	NPC41847
0.8138	Intermediate Similarity	NPC34070
0.8138	Intermediate Similarity	NPC469526
0.8137	Intermediate Similarity	NPC294965
0.8137	Intermediate Similarity	NPC206605
0.8137	Intermediate Similarity	NPC215612
0.8129	Intermediate Similarity	NPC38545

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 NPC476535 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	889
0.2-0.3	1651
0.3-0.4	2944
0.4-0.5	2004
0.5-0.6	949
0.6-0.7	323
0.7-0.8	48
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8716	High Similarity	NPD7422	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD943	Approved
0.8039	Intermediate Similarity	NPD7390	Discontinued
0.8038	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD2801	Approved
0.7914	Intermediate Similarity	NPD6232	Discontinued
0.7879	Intermediate Similarity	NPD7473	Discontinued
0.775	Intermediate Similarity	NPD1934	Approved
0.7724	Intermediate Similarity	NPD1470	Approved
0.7697	Intermediate Similarity	NPD5408	Approved
0.7697	Intermediate Similarity	NPD5405	Approved
0.7697	Intermediate Similarity	NPD5406	Approved
0.7697	Intermediate Similarity	NPD5404	Approved
0.7692	Intermediate Similarity	NPD1201	Approved
0.7582	Intermediate Similarity	NPD2935	Discontinued
0.758	Intermediate Similarity	NPD1511	Approved
0.7576	Intermediate Similarity	NPD5494	Approved
0.755	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD2534	Approved
0.7532	Intermediate Similarity	NPD2533	Approved
0.7532	Intermediate Similarity	NPD2532	Approved
0.7517	Intermediate Similarity	NPD9269	Phase 2
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8166	Discontinued
0.7484	Intermediate Similarity	NPD1512	Approved
0.7471	Intermediate Similarity	NPD5844	Phase 1
0.7425	Intermediate Similarity	NPD6959	Discontinued
0.7421	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6234	Discontinued
0.7407	Intermediate Similarity	NPD4380	Phase 2
0.7405	Intermediate Similarity	NPD3300	Phase 2
0.7372	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD37	Approved
0.731	Intermediate Similarity	NPD3019	Approved
0.731	Intermediate Similarity	NPD3818	Discontinued
0.729	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD7819	Suspended
0.7247	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6559	Discontinued
0.7241	Intermediate Similarity	NPD9268	Approved
0.7229	Intermediate Similarity	NPD3817	Phase 2
0.7225	Intermediate Similarity	NPD7074	Phase 3
0.7215	Intermediate Similarity	NPD2800	Approved
0.72	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2932	Approved
0.7186	Intermediate Similarity	NPD4966	Approved
0.7186	Intermediate Similarity	NPD4967	Phase 2
0.7186	Intermediate Similarity	NPD7768	Phase 2
0.7186	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD7054	Approved
0.7161	Intermediate Similarity	NPD6651	Approved
0.7161	Intermediate Similarity	NPD1607	Approved
0.7143	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7133	Intermediate Similarity	NPD1164	Approved
0.7133	Intermediate Similarity	NPD3094	Phase 2
0.7126	Intermediate Similarity	NPD7472	Approved
0.7125	Intermediate Similarity	NPD6190	Approved
0.7118	Intermediate Similarity	NPD1247	Approved
0.711	Intermediate Similarity	NPD7228	Approved
0.7099	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6599	Discontinued
0.7089	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6797	Phase 2
0.7066	Intermediate Similarity	NPD1465	Phase 2
0.7066	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7411	Suspended
0.7045	Intermediate Similarity	NPD7251	Discontinued
0.7044	Intermediate Similarity	NPD1549	Phase 2
0.7039	Intermediate Similarity	NPD8150	Discontinued
0.7034	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6100	Approved
0.7025	Intermediate Similarity	NPD6099	Approved
0.7025	Intermediate Similarity	NPD1551	Phase 2
0.7024	Intermediate Similarity	NPD5402	Approved
0.7021	Intermediate Similarity	NPD4750	Phase 3
0.7021	Intermediate Similarity	NPD3022	Approved
0.7021	Intermediate Similarity	NPD3021	Approved
0.7007	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3092	Approved
0.6978	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5710	Approved
0.6977	Remote Similarity	NPD5711	Approved
0.6968	Remote Similarity	NPD6663	Approved
0.6962	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7003	Approved
0.6948	Remote Similarity	NPD3027	Phase 3
0.6941	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3226	Approved
0.6928	Remote Similarity	NPD5736	Approved
0.6928	Remote Similarity	NPD9494	Approved
0.6918	Remote Similarity	NPD2796	Approved
0.6913	Remote Similarity	NPD3026	Approved
0.6913	Remote Similarity	NPD3023	Approved
0.691	Remote Similarity	NPD7808	Phase 3
0.6905	Remote Similarity	NPD6801	Discontinued
0.6897	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3024	Approved
0.6892	Remote Similarity	NPD3025	Approved
0.6889	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2346	Discontinued
0.6875	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2799	Discontinued
0.6852	Remote Similarity	NPD3750	Approved
0.6852	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD8434	Phase 2
0.6829	Remote Similarity	NPD6799	Approved
0.6826	Remote Similarity	NPD7458	Discontinued
0.6824	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3091	Approved
0.6818	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5028	Approved
0.6816	Remote Similarity	NPD5026	Approved
0.6816	Remote Similarity	NPD4954	Approved
0.6816	Remote Similarity	NPD4955	Approved
0.6816	Remote Similarity	NPD36	Approved
0.6816	Remote Similarity	NPD5034	Approved
0.6815	Remote Similarity	NPD1613	Approved
0.6815	Remote Similarity	NPD3620	Phase 2
0.6815	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6534	Approved
0.6811	Remote Similarity	NPD6535	Approved
0.6802	Remote Similarity	NPD919	Approved
0.6795	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3764	Approved
0.6778	Remote Similarity	NPD8313	Approved
0.6778	Remote Similarity	NPD8312	Approved
0.6774	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD447	Suspended
0.6765	Remote Similarity	NPD5761	Phase 2
0.6765	Remote Similarity	NPD5760	Phase 2
0.676	Remote Similarity	NPD5030	Phase 2
0.6759	Remote Similarity	NPD7635	Approved
0.6758	Remote Similarity	NPD5038	Approved
0.6758	Remote Similarity	NPD5037	Approved
0.6753	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4628	Phase 3
0.6744	Remote Similarity	NPD3749	Approved
0.6726	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7199	Phase 2
0.6724	Remote Similarity	NPD8127	Discontinued
0.672	Remote Similarity	NPD6780	Approved
0.672	Remote Similarity	NPD6779	Approved
0.672	Remote Similarity	NPD6777	Approved
0.672	Remote Similarity	NPD6782	Approved
0.672	Remote Similarity	NPD6778	Approved
0.672	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6776	Approved
0.672	Remote Similarity	NPD6781	Approved
0.6707	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD920	Approved
0.6703	Remote Similarity	NPD5036	Approved
0.6702	Remote Similarity	NPD7700	Phase 2
0.6702	Remote Similarity	NPD7699	Phase 2
0.6689	Remote Similarity	NPD9493	Approved
0.6688	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6020	Phase 2
0.6685	Remote Similarity	NPD5035	Approved
0.6667	Remote Similarity	NPD5029	Approved
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD7240	Approved
0.6667	Remote Similarity	NPD5031	Approved
0.6667	Remote Similarity	NPD5951	Approved
0.6667	Remote Similarity	NPD5027	Approved
0.6649	Remote Similarity	NPD6823	Phase 2
0.6648	Remote Similarity	NPD3926	Phase 2
0.6648	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6273	Approved
0.6645	Remote Similarity	NPD2798	Approved
0.6643	Remote Similarity	NPD940	Approved
0.6643	Remote Similarity	NPD846	Approved
0.663	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3095	Discontinued
0.6615	Remote Similarity	NPD7435	Discontinued
0.6615	Remote Similarity	NPD8151	Discontinued
0.6607	Remote Similarity	NPD5403	Approved
0.6597	Remote Similarity	NPD74	Approved
0.6597	Remote Similarity	NPD9266	Approved
0.6591	Remote Similarity	NPD7229	Phase 3
0.6587	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2313	Discontinued
0.6578	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6213	Phase 3
0.6578	Remote Similarity	NPD6212	Phase 3
0.6571	Remote Similarity	NPD289	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