NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.17
Volume:	280.771
LogP:	1.195
LogD:	1.166
LogS:	-2.42
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	4.954
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.978
MDCK Permeability:	3.191479481756687e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.937
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.398
Plasma Protein Binding (PPB):	69.27648162841797%
Volume Distribution (VD):	0.975
Pgp-substrate:	37.0069694519043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	4.829
Half-life (T1/2):	0.57

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.314
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.238
Rat Oral Acute Toxicity:	0.836
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.52
Carcinogencity:	0.082
Eye Corrosion:	0.27
Eye Irritation:	0.319
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC232156

Natural Product ID:	NPC232156
*Common Name:**	7-Hydroxydeacetylbotryenalol
IUPAC Name:	(2R,3S,5R,7S,7aR)-2,7-dihydroxy-3-(hydroxymethyl)-1,1,3,5-tetramethyl-5,6,7,7a-tetrahydro-2H-indene-4-carbaldehyde
Synonyms:	7-Hydroxydeacetylbotryenalol
Standard InCHIKey:	HFLYKFYHNXRCFY-ZAFNGOSVSA-N
Standard InCHI:	InChI=1S/C15H24O4/c1-8-5-10(18)12-11(9(8)6-16)15(4,7-17)13(19)14(12,2)3/h6,8,10,12-13,17-19H,5,7H2,1-4H3/t8-,10+,12-,13-,15-/m1/s1
SMILES:	C[C@@H]1C[C@@H]([C@@H]2C(=C1C=O)[C@@](C)(CO)[C@@H](C2(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517702
PubChem CID:	11334679
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols 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
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	isolated from the marine red alga Polysiphonia	n.a.	PMID[15787444]
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917307]

☑ 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
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	0.0	mm	PMID[565995]
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	6.0	mm	PMID[565995]

☑ 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 NPC232156 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	198
0.1-0.2	1636
0.2-0.3	6508
0.3-0.4	15590
0.4-0.5	7768
0.5-0.6	7910
0.6-0.7	2801
0.7-0.8	280
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8276	Intermediate Similarity	NPC36350
0.8111	Intermediate Similarity	NPC97032
0.7957	Intermediate Similarity	NPC111015
0.7927	Intermediate Similarity	NPC310608
0.7895	Intermediate Similarity	NPC18509
0.7895	Intermediate Similarity	NPC190554
0.7872	Intermediate Similarity	NPC48330
0.7872	Intermediate Similarity	NPC200702
0.7865	Intermediate Similarity	NPC197823
0.7857	Intermediate Similarity	NPC55872
0.7849	Intermediate Similarity	NPC109414
0.7826	Intermediate Similarity	NPC183283
0.7791	Intermediate Similarity	NPC261125
0.7791	Intermediate Similarity	NPC181195
0.7789	Intermediate Similarity	NPC173272
0.7789	Intermediate Similarity	NPC95565
0.7778	Intermediate Similarity	NPC28656
0.7732	Intermediate Similarity	NPC144956
0.7732	Intermediate Similarity	NPC15390
0.7723	Intermediate Similarity	NPC65941
0.7717	Intermediate Similarity	NPC77263
0.7717	Intermediate Similarity	NPC250592
0.7717	Intermediate Similarity	NPC186688
0.7711	Intermediate Similarity	NPC261316
0.7711	Intermediate Similarity	NPC49737
0.7684	Intermediate Similarity	NPC472485
0.7684	Intermediate Similarity	NPC472932
0.766	Intermediate Similarity	NPC25750
0.766	Intermediate Similarity	NPC206810
0.7647	Intermediate Similarity	NPC242722
0.764	Intermediate Similarity	NPC474748
0.764	Intermediate Similarity	NPC476082
0.764	Intermediate Similarity	NPC278648
0.7634	Intermediate Similarity	NPC477711
0.7629	Intermediate Similarity	NPC114274
0.7624	Intermediate Similarity	NPC475060
0.7624	Intermediate Similarity	NPC83744
0.7624	Intermediate Similarity	NPC220229
0.7614	Intermediate Similarity	NPC136150
0.7609	Intermediate Similarity	NPC328539
0.7609	Intermediate Similarity	NPC143767
0.7609	Intermediate Similarity	NPC131470
0.7604	Intermediate Similarity	NPC192428
0.7604	Intermediate Similarity	NPC477853
0.7604	Intermediate Similarity	NPC49371
0.7579	Intermediate Similarity	NPC245972
0.7579	Intermediate Similarity	NPC166906
0.7579	Intermediate Similarity	NPC196485
0.7579	Intermediate Similarity	NPC298919
0.7558	Intermediate Similarity	NPC276769
0.7553	Intermediate Similarity	NPC99380
0.7553	Intermediate Similarity	NPC185936
0.7553	Intermediate Similarity	NPC168027
0.7553	Intermediate Similarity	NPC155304
0.7551	Intermediate Similarity	NPC83709
0.7551	Intermediate Similarity	NPC154072
0.7551	Intermediate Similarity	NPC474720
0.7549	Intermediate Similarity	NPC217201
0.7549	Intermediate Similarity	NPC329417
0.7527	Intermediate Similarity	NPC1015
0.7527	Intermediate Similarity	NPC275740
0.7527	Intermediate Similarity	NPC477943
0.7527	Intermediate Similarity	NPC31985
0.7527	Intermediate Similarity	NPC86319
0.7526	Intermediate Similarity	NPC69385
0.7526	Intermediate Similarity	NPC18319
0.7525	Intermediate Similarity	NPC260268
0.7525	Intermediate Similarity	NPC296945
0.7525	Intermediate Similarity	NPC319077
0.7525	Intermediate Similarity	NPC149047
0.7525	Intermediate Similarity	NPC50692
0.7525	Intermediate Similarity	NPC202167
0.7525	Intermediate Similarity	NPC85829
0.7525	Intermediate Similarity	NPC171137
0.7525	Intermediate Similarity	NPC152695
0.7525	Intermediate Similarity	NPC150531
0.7525	Intermediate Similarity	NPC214264
0.7525	Intermediate Similarity	NPC48733
0.7525	Intermediate Similarity	NPC302607
0.7525	Intermediate Similarity	NPC49958
0.7525	Intermediate Similarity	NPC97202
0.7525	Intermediate Similarity	NPC476027
0.75	Intermediate Similarity	NPC241156
0.75	Intermediate Similarity	NPC472493
0.75	Intermediate Similarity	NPC37408
0.75	Intermediate Similarity	NPC317586
0.75	Intermediate Similarity	NPC470016
0.75	Intermediate Similarity	NPC472824
0.75	Intermediate Similarity	NPC191892
0.7476	Intermediate Similarity	NPC11710
0.7475	Intermediate Similarity	NPC237190
0.7474	Intermediate Similarity	NPC125180
0.7474	Intermediate Similarity	NPC250575
0.7473	Intermediate Similarity	NPC202868
0.747	Intermediate Similarity	NPC173321
0.7451	Intermediate Similarity	NPC477916
0.7449	Intermediate Similarity	NPC10364
0.7449	Intermediate Similarity	NPC222011
0.7449	Intermediate Similarity	NPC477854
0.7447	Intermediate Similarity	NPC191684
0.7447	Intermediate Similarity	NPC136801
0.7444	Intermediate Similarity	NPC64600
0.7444	Intermediate Similarity	NPC62214
0.7442	Intermediate Similarity	NPC124289
0.7442	Intermediate Similarity	NPC115719
0.7442	Intermediate Similarity	NPC141346
0.7442	Intermediate Similarity	NPC25908
0.7442	Intermediate Similarity	NPC142759
0.7442	Intermediate Similarity	NPC473437
0.7426	Intermediate Similarity	NPC204833
0.7426	Intermediate Similarity	NPC470838
0.7426	Intermediate Similarity	NPC209502
0.7426	Intermediate Similarity	NPC477812
0.7423	Intermediate Similarity	NPC305483
0.7423	Intermediate Similarity	NPC264979
0.7423	Intermediate Similarity	NPC328162
0.7423	Intermediate Similarity	NPC96859
0.7423	Intermediate Similarity	NPC135548
0.7423	Intermediate Similarity	NPC125622
0.7419	Intermediate Similarity	NPC471722
0.7419	Intermediate Similarity	NPC477710
0.7412	Intermediate Similarity	NPC102313
0.7412	Intermediate Similarity	NPC199316
0.7404	Intermediate Similarity	NPC197428
0.7404	Intermediate Similarity	NPC235077
0.74	Intermediate Similarity	NPC22388
0.74	Intermediate Similarity	NPC473424
0.7396	Intermediate Similarity	NPC280804
0.7396	Intermediate Similarity	NPC196227
0.7391	Intermediate Similarity	NPC472494
0.7391	Intermediate Similarity	NPC212843
0.7391	Intermediate Similarity	NPC474732
0.7391	Intermediate Similarity	NPC72133
0.7391	Intermediate Similarity	NPC472491
0.7391	Intermediate Similarity	NPC474733
0.7391	Intermediate Similarity	NPC145879
0.7391	Intermediate Similarity	NPC31564
0.7391	Intermediate Similarity	NPC474778
0.7391	Intermediate Similarity	NPC183736
0.7391	Intermediate Similarity	NPC94755
0.7386	Intermediate Similarity	NPC246458
0.7386	Intermediate Similarity	NPC229204
0.7379	Intermediate Similarity	NPC177064
0.7374	Intermediate Similarity	NPC205899
0.7368	Intermediate Similarity	NPC233116
0.7368	Intermediate Similarity	NPC63748
0.7368	Intermediate Similarity	NPC23434
0.7368	Intermediate Similarity	NPC131872
0.7363	Intermediate Similarity	NPC58841
0.7363	Intermediate Similarity	NPC329043
0.7363	Intermediate Similarity	NPC321187
0.7363	Intermediate Similarity	NPC470812
0.7363	Intermediate Similarity	NPC161423
0.7363	Intermediate Similarity	NPC227064
0.7358	Intermediate Similarity	NPC73300
0.7358	Intermediate Similarity	NPC194100
0.7358	Intermediate Similarity	NPC108721
0.7353	Intermediate Similarity	NPC231530
0.7353	Intermediate Similarity	NPC323834
0.7353	Intermediate Similarity	NPC278628
0.7353	Intermediate Similarity	NPC257353
0.7347	Intermediate Similarity	NPC320306
0.7347	Intermediate Similarity	NPC108078
0.7347	Intermediate Similarity	NPC43747
0.734	Intermediate Similarity	NPC123912
0.734	Intermediate Similarity	NPC326627
0.734	Intermediate Similarity	NPC473100
0.734	Intermediate Similarity	NPC232747
0.734	Intermediate Similarity	NPC310010
0.7333	Intermediate Similarity	NPC133844
0.7327	Intermediate Similarity	NPC470839
0.7327	Intermediate Similarity	NPC311612
0.7327	Intermediate Similarity	NPC270046
0.7327	Intermediate Similarity	NPC117185
0.7327	Intermediate Similarity	NPC159442
0.7327	Intermediate Similarity	NPC251017
0.732	Intermediate Similarity	NPC297199
0.732	Intermediate Similarity	NPC473170
0.732	Intermediate Similarity	NPC127063
0.732	Intermediate Similarity	NPC138245
0.732	Intermediate Similarity	NPC255809
0.732	Intermediate Similarity	NPC469873
0.732	Intermediate Similarity	NPC231060
0.732	Intermediate Similarity	NPC279313
0.732	Intermediate Similarity	NPC84018
0.732	Intermediate Similarity	NPC29112
0.7312	Intermediate Similarity	NPC475740
0.7312	Intermediate Similarity	NPC312215
0.7312	Intermediate Similarity	NPC58063
0.7292	Intermediate Similarity	NPC470375
0.7292	Intermediate Similarity	NPC477435
0.7292	Intermediate Similarity	NPC181594
0.7292	Intermediate Similarity	NPC475255
0.7292	Intermediate Similarity	NPC477436
0.7292	Intermediate Similarity	NPC470376
0.7292	Intermediate Similarity	NPC472930
0.7292	Intermediate Similarity	NPC59350
0.7292	Intermediate Similarity	NPC69454
0.7292	Intermediate Similarity	NPC144739
0.7292	Intermediate Similarity	NPC477855

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 NPC232156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	2408
0.2-0.3	4031
0.3-0.4	1761
0.4-0.5	363
0.5-0.6	197
0.6-0.7	178
0.7-0.8	10
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
0.7895	Intermediate Similarity	NPD4755	Approved
0.7732	Intermediate Similarity	NPD4700	Approved
0.7732	Intermediate Similarity	NPD4696	Approved
0.7732	Intermediate Similarity	NPD5285	Approved
0.7732	Intermediate Similarity	NPD5286	Approved
0.7604	Intermediate Similarity	NPD4697	Phase 3
0.7576	Intermediate Similarity	NPD5211	Phase 2
0.7576	Intermediate Similarity	NPD5225	Approved
0.7576	Intermediate Similarity	NPD5224	Approved
0.7576	Intermediate Similarity	NPD5226	Approved
0.7576	Intermediate Similarity	NPD4633	Approved
0.7527	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.7475	Intermediate Similarity	NPD5223	Approved
0.7474	Intermediate Similarity	NPD4202	Approved
0.7426	Intermediate Similarity	NPD5141	Approved
0.7404	Intermediate Similarity	NPD4634	Approved
0.7368	Intermediate Similarity	NPD6079	Approved
0.7363	Intermediate Similarity	NPD3665	Phase 1
0.7363	Intermediate Similarity	NPD3666	Approved
0.7363	Intermediate Similarity	NPD3133	Approved
0.7353	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD6402	Approved
0.7353	Intermediate Similarity	NPD7128	Approved
0.7353	Intermediate Similarity	NPD5739	Approved
0.7353	Intermediate Similarity	NPD4767	Approved
0.7353	Intermediate Similarity	NPD4768	Approved
0.734	Intermediate Similarity	NPD4753	Phase 2
0.7327	Intermediate Similarity	NPD4754	Approved
0.7282	Intermediate Similarity	NPD5701	Approved
0.7282	Intermediate Similarity	NPD5697	Approved
0.7245	Intermediate Similarity	NPD5222	Approved
0.7245	Intermediate Similarity	NPD5221	Approved
0.7245	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6899	Approved
0.7212	Intermediate Similarity	NPD4730	Approved
0.7212	Intermediate Similarity	NPD4729	Approved
0.7212	Intermediate Similarity	NPD6881	Approved
0.7212	Intermediate Similarity	NPD5128	Approved
0.7212	Intermediate Similarity	NPD7320	Approved
0.7204	Intermediate Similarity	NPD3618	Phase 1
0.7174	Intermediate Similarity	NPD4786	Approved
0.7172	Intermediate Similarity	NPD5173	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7075	Intermediate Similarity	NPD5250	Approved
0.7075	Intermediate Similarity	NPD5251	Approved
0.7075	Intermediate Similarity	NPD5248	Approved
0.7075	Intermediate Similarity	NPD7290	Approved
0.7075	Intermediate Similarity	NPD5249	Phase 3
0.7075	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD6883	Approved
0.7075	Intermediate Similarity	NPD5247	Approved
0.7048	Intermediate Similarity	NPD6011	Approved
0.7037	Intermediate Similarity	NPD4632	Approved
0.7021	Intermediate Similarity	NPD5279	Phase 3
0.7019	Intermediate Similarity	NPD6008	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD5215	Approved
0.7009	Intermediate Similarity	NPD6617	Approved
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD5217	Approved
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD5216	Approved
0.697	Remote Similarity	NPD5210	Approved
0.697	Remote Similarity	NPD4629	Approved
0.6957	Remote Similarity	NPD4221	Approved
0.6957	Remote Similarity	NPD4223	Phase 3
0.6944	Remote Similarity	NPD8297	Approved
0.6944	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD5368	Approved
0.6916	Remote Similarity	NPD5169	Approved
0.6916	Remote Similarity	NPD5135	Approved
0.6916	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5127	Approved
0.6847	Remote Similarity	NPD6009	Approved
0.6832	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD6083	Phase 2
0.6814	Remote Similarity	NPD6319	Approved
0.6814	Remote Similarity	NPD6054	Approved
0.6814	Remote Similarity	NPD6059	Approved
0.6809	Remote Similarity	NPD4197	Approved
0.68	Remote Similarity	NPD5695	Phase 3
0.6792	Remote Similarity	NPD6412	Phase 2
0.6789	Remote Similarity	NPD6053	Discontinued
0.6774	Remote Similarity	NPD6435	Approved
0.6768	Remote Similarity	NPD6399	Phase 3
0.6757	Remote Similarity	NPD6274	Approved
0.6754	Remote Similarity	NPD6015	Approved
0.6754	Remote Similarity	NPD6016	Approved
0.6739	Remote Similarity	NPD4748	Discontinued
0.6737	Remote Similarity	NPD5329	Approved
0.6703	Remote Similarity	NPD3617	Approved
0.6701	Remote Similarity	NPD4518	Approved
0.6696	Remote Similarity	NPD6370	Approved
0.6696	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD5284	Approved
0.6632	Remote Similarity	NPD3668	Phase 3
0.6609	Remote Similarity	NPD5983	Phase 2
0.6602	Remote Similarity	NPD7638	Approved
0.6602	Remote Similarity	NPD5696	Approved
0.66	Remote Similarity	NPD5778	Approved
0.66	Remote Similarity	NPD5779	Approved
0.6581	Remote Similarity	NPD7492	Approved
0.6579	Remote Similarity	NPD7100	Approved
0.6579	Remote Similarity	NPD7101	Approved
0.6574	Remote Similarity	NPD5168	Approved
0.6556	Remote Similarity	NPD3703	Phase 2
0.6549	Remote Similarity	NPD6317	Approved
0.6538	Remote Similarity	NPD7640	Approved
0.6538	Remote Similarity	NPD7639	Approved
0.6535	Remote Similarity	NPD5282	Discontinued
0.6526	Remote Similarity	NPD4788	Approved
0.6526	Remote Similarity	NPD5362	Discontinued
0.6525	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD7515	Phase 2
0.65	Remote Similarity	NPD7319	Approved
0.6496	Remote Similarity	NPD7604	Phase 2
0.6495	Remote Similarity	NPD7521	Approved
0.6495	Remote Similarity	NPD7334	Approved
0.6495	Remote Similarity	NPD5330	Approved
0.6495	Remote Similarity	NPD7146	Approved
0.6495	Remote Similarity	NPD6409	Approved
0.6495	Remote Similarity	NPD6684	Approved
0.6491	Remote Similarity	NPD6313	Approved
0.6491	Remote Similarity	NPD6335	Approved
0.6491	Remote Similarity	NPD6314	Approved
0.6471	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8293	Discontinued
0.6471	Remote Similarity	NPD7078	Approved
0.6466	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD6909	Approved
0.6465	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6101	Approved
0.6458	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6929	Approved
0.6429	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7736	Approved
0.6415	Remote Similarity	NPD7632	Discontinued
0.64	Remote Similarity	NPD5785	Approved
0.64	Remote Similarity	NPD4096	Approved
0.6392	Remote Similarity	NPD1696	Phase 3
0.6392	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5363	Approved
0.6387	Remote Similarity	NPD6336	Discontinued
0.6383	Remote Similarity	NPD7525	Registered
0.6383	Remote Similarity	NPD4695	Discontinued
0.6383	Remote Similarity	NPD4820	Approved
0.6383	Remote Similarity	NPD4821	Approved
0.6383	Remote Similarity	NPD6930	Phase 2
0.6383	Remote Similarity	NPD4819	Approved
0.6383	Remote Similarity	NPD6931	Approved
0.6383	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4822	Approved
0.6374	Remote Similarity	NPD7339	Approved
0.6374	Remote Similarity	NPD6942	Approved
0.6364	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6695	Phase 3
0.6344	Remote Similarity	NPD4268	Approved
0.6344	Remote Similarity	NPD6114	Approved
0.6344	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6697	Approved
0.6344	Remote Similarity	NPD6115	Approved
0.6344	Remote Similarity	NPD6118	Approved
0.6344	Remote Similarity	NPD4271	Approved
0.6327	Remote Similarity	NPD5786	Approved
0.6325	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5369	Approved
0.6293	Remote Similarity	NPD4522	Approved
0.6281	Remote Similarity	NPD6033	Approved
0.6277	Remote Similarity	NPD4195	Approved
0.6275	Remote Similarity	NPD5133	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