NPASS Compound

Structure

NPC92226 OpenBabel07101718182D 23 25 0 0 1 0 0 0 0 0999 V2000 5.2209 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 2.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3564 1.9729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2573 1.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9944 0.1495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 0.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4311 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 1.4010 0.0000 C 0 0 1 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 4.3548 -0.0990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1934 0.5747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1490 0.9888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 20 1 6 0 0 0 19 22 1 6 0 0 0 20 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	3.376
LogD:	2.985
LogS:	-4.528
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.727
Synthetic Accessibility Score:	4.699
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.643
MDCK Permeability:	1.455633628211217e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.091
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.771
Plasma Protein Binding (PPB):	85.3078384399414%
Volume Distribution (VD):	1.432
Pgp-substrate:	13.025468826293945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.7
CYP2C19-inhibitor:	0.53
CYP2C19-substrate:	0.728
CYP2C9-inhibitor:	0.386
CYP2C9-substrate:	0.396
CYP2D6-inhibitor:	0.086
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.615
CYP3A4-substrate:	0.71

ADMET: Excretion

Clearance (CL):	4.763
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.178
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.834
Skin Sensitization:	0.664
Carcinogencity:	0.774
Eye Corrosion:	0.147
Eye Irritation:	0.964
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC92226

Natural Product ID:	NPC92226
*Common Name:**	8Beta,10Beta-Dihydroxyicetexa-9(11),13-Dien-12-One
IUPAC Name:	(4aR,6aS,10aS)-4a,10a-dihydroxy-7,7-dimethyl-3-propan-2-yl-6,6a,8,9,10,11-hexahydro-5H-dibenzo[3,1-a:1',4'-e][7]annulen-2-one
Synonyms:
Standard InCHIKey:	OZULRQMDNJXVDJ-SXLOBPIMSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13(2)15-12-19(22)9-6-17-18(3,4)7-5-8-20(17,23)11-14(19)10-16(15)21/h10,12-13,17,22-23H,5-9,11H2,1-4H3/t17-,19+,20-/m0/s1
SMILES:	CC(C1=C[C@]2(O)CC[C@@H]3[C@](CC2=CC1=O)(O)CCCC3(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385635
PubChem CID:	71725859
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32847	fokienia hodginsii	Species	Cupressaceae	Eukaryota	Twigs and Leaves	n.a.	n.a.	PMID[23691952]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[465907]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[465907]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[465907]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[465907]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[465907]

☑ 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 NPC92226 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	179
0.1-0.2	1342
0.2-0.3	5450
0.3-0.4	13515
0.4-0.5	11373
0.5-0.6	7060
0.6-0.7	3418
0.7-0.8	358
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8625	High Similarity	NPC170394
0.8193	Intermediate Similarity	NPC226068
0.8148	Intermediate Similarity	NPC34110
0.8148	Intermediate Similarity	NPC266193
0.8148	Intermediate Similarity	NPC257666
0.814	Intermediate Similarity	NPC472985
0.814	Intermediate Similarity	NPC472986
0.814	Intermediate Similarity	NPC472974
0.8101	Intermediate Similarity	NPC247586
0.8049	Intermediate Similarity	NPC275494
0.8049	Intermediate Similarity	NPC471409
0.8025	Intermediate Similarity	NPC472305
0.8	Intermediate Similarity	NPC22134
0.7955	Intermediate Similarity	NPC48107
0.7955	Intermediate Similarity	NPC58271
0.7952	Intermediate Similarity	NPC308038
0.7927	Intermediate Similarity	NPC203403
0.7927	Intermediate Similarity	NPC97377
0.7927	Intermediate Similarity	NPC132542
0.7912	Intermediate Similarity	NPC196227
0.7907	Intermediate Similarity	NPC476412
0.7889	Intermediate Similarity	NPC116726
0.7865	Intermediate Similarity	NPC472983
0.7865	Intermediate Similarity	NPC472676
0.7865	Intermediate Similarity	NPC472973
0.7865	Intermediate Similarity	NPC472688
0.7865	Intermediate Similarity	NPC314727
0.7865	Intermediate Similarity	NPC474918
0.7857	Intermediate Similarity	NPC472301
0.7857	Intermediate Similarity	NPC476809
0.7831	Intermediate Similarity	NPC475994
0.7831	Intermediate Similarity	NPC62336
0.7831	Intermediate Similarity	NPC207772
0.7805	Intermediate Similarity	NPC7629
0.7805	Intermediate Similarity	NPC186554
0.7805	Intermediate Similarity	NPC250621
0.7805	Intermediate Similarity	NPC76966
0.7805	Intermediate Similarity	NPC263582
0.7805	Intermediate Similarity	NPC151622
0.7765	Intermediate Similarity	NPC473217
0.7765	Intermediate Similarity	NPC6663
0.7753	Intermediate Similarity	NPC471791
0.7753	Intermediate Similarity	NPC471793
0.7738	Intermediate Similarity	NPC281138
0.7738	Intermediate Similarity	NPC470429
0.7717	Intermediate Similarity	NPC472976
0.7717	Intermediate Similarity	NPC472977
0.7717	Intermediate Similarity	NPC119562
0.7717	Intermediate Similarity	NPC279410
0.7711	Intermediate Similarity	NPC85105
0.7711	Intermediate Similarity	NPC149550
0.7701	Intermediate Similarity	NPC251170
0.7701	Intermediate Similarity	NPC40687
0.7692	Intermediate Similarity	NPC73457
0.7692	Intermediate Similarity	NPC472978
0.7683	Intermediate Similarity	NPC32832
0.7674	Intermediate Similarity	NPC38796
0.7674	Intermediate Similarity	NPC93590
0.7674	Intermediate Similarity	NPC158411
0.7667	Intermediate Similarity	NPC36668
0.7667	Intermediate Similarity	NPC473100
0.7667	Intermediate Similarity	NPC118011
0.7647	Intermediate Similarity	NPC471514
0.7647	Intermediate Similarity	NPC108955
0.7647	Intermediate Similarity	NPC96362
0.7647	Intermediate Similarity	NPC172013
0.7647	Intermediate Similarity	NPC157895
0.7647	Intermediate Similarity	NPC148685
0.7647	Intermediate Similarity	NPC469637
0.7647	Intermediate Similarity	NPC104120
0.764	Intermediate Similarity	NPC471792
0.764	Intermediate Similarity	NPC476409
0.7634	Intermediate Similarity	NPC476245
0.7634	Intermediate Similarity	NPC271195
0.7632	Intermediate Similarity	NPC81615
0.7619	Intermediate Similarity	NPC198240
0.7614	Intermediate Similarity	NPC476426
0.759	Intermediate Similarity	NPC1973
0.759	Intermediate Similarity	NPC470525
0.759	Intermediate Similarity	NPC167873
0.7586	Intermediate Similarity	NPC169941
0.7586	Intermediate Similarity	NPC251475
0.7586	Intermediate Similarity	NPC49019
0.7582	Intermediate Similarity	NPC38952
0.7582	Intermediate Similarity	NPC473099
0.7582	Intermediate Similarity	NPC134321
0.7561	Intermediate Similarity	NPC215050
0.7561	Intermediate Similarity	NPC78527
0.7558	Intermediate Similarity	NPC476646
0.7558	Intermediate Similarity	NPC55869
0.7558	Intermediate Similarity	NPC159148
0.7556	Intermediate Similarity	NPC72397
0.7531	Intermediate Similarity	NPC84790
0.7528	Intermediate Similarity	NPC194417
0.7528	Intermediate Similarity	NPC473226
0.7528	Intermediate Similarity	NPC470955
0.7528	Intermediate Similarity	NPC471219
0.7528	Intermediate Similarity	NPC470415
0.7528	Intermediate Similarity	NPC239685
0.7527	Intermediate Similarity	NPC57117
0.75	Intermediate Similarity	NPC136473
0.75	Intermediate Similarity	NPC61952
0.75	Intermediate Similarity	NPC74995
0.75	Intermediate Similarity	NPC165711
0.75	Intermediate Similarity	NPC233116
0.75	Intermediate Similarity	NPC472975
0.75	Intermediate Similarity	NPC197659
0.75	Intermediate Similarity	NPC154072
0.75	Intermediate Similarity	NPC470428
0.7474	Intermediate Similarity	NPC135685
0.7474	Intermediate Similarity	NPC287668
0.7474	Intermediate Similarity	NPC470522
0.7474	Intermediate Similarity	NPC170131
0.7474	Intermediate Similarity	NPC99726
0.7471	Intermediate Similarity	NPC2524
0.747	Intermediate Similarity	NPC476795
0.7468	Intermediate Similarity	NPC263161
0.7449	Intermediate Similarity	NPC230918
0.7449	Intermediate Similarity	NPC131366
0.7444	Intermediate Similarity	NPC231599
0.7442	Intermediate Similarity	NPC138492
0.7442	Intermediate Similarity	NPC233352
0.7442	Intermediate Similarity	NPC824
0.7442	Intermediate Similarity	NPC281880
0.7442	Intermediate Similarity	NPC2482
0.7439	Intermediate Similarity	NPC153660
0.7423	Intermediate Similarity	NPC115862
0.7423	Intermediate Similarity	NPC470184
0.7419	Intermediate Similarity	NPC109305
0.7419	Intermediate Similarity	NPC131840
0.7419	Intermediate Similarity	NPC476416
0.7416	Intermediate Similarity	NPC471267
0.7416	Intermediate Similarity	NPC109528
0.7416	Intermediate Similarity	NPC70685
0.7412	Intermediate Similarity	NPC74410
0.7412	Intermediate Similarity	NPC189485
0.7412	Intermediate Similarity	NPC297996
0.7412	Intermediate Similarity	NPC19443
0.7412	Intermediate Similarity	NPC476949
0.7412	Intermediate Similarity	NPC253561
0.7412	Intermediate Similarity	NPC80088
0.7412	Intermediate Similarity	NPC179028
0.7396	Intermediate Similarity	NPC316598
0.7396	Intermediate Similarity	NPC103051
0.7391	Intermediate Similarity	NPC230332
0.7391	Intermediate Similarity	NPC48010
0.7391	Intermediate Similarity	NPC128672
0.7391	Intermediate Similarity	NPC212369
0.7391	Intermediate Similarity	NPC19771
0.7386	Intermediate Similarity	NPC57370
0.7386	Intermediate Similarity	NPC97913
0.7386	Intermediate Similarity	NPC105173
0.7386	Intermediate Similarity	NPC297398
0.7386	Intermediate Similarity	NPC64600
0.7386	Intermediate Similarity	NPC476927
0.7386	Intermediate Similarity	NPC79945
0.7381	Intermediate Similarity	NPC253190
0.7381	Intermediate Similarity	NPC180886
0.7381	Intermediate Similarity	NPC265588
0.7368	Intermediate Similarity	NPC202833
0.7368	Intermediate Similarity	NPC117133
0.7363	Intermediate Similarity	NPC124927
0.7363	Intermediate Similarity	NPC475101
0.7363	Intermediate Similarity	NPC472802
0.7363	Intermediate Similarity	NPC104560
0.7363	Intermediate Similarity	NPC476427
0.7356	Intermediate Similarity	NPC249423
0.7356	Intermediate Similarity	NPC119229
0.7356	Intermediate Similarity	NPC225515
0.7356	Intermediate Similarity	NPC278459
0.7356	Intermediate Similarity	NPC121984
0.7356	Intermediate Similarity	NPC136150
0.7349	Intermediate Similarity	NPC306727
0.7349	Intermediate Similarity	NPC201048
0.7349	Intermediate Similarity	NPC476366
0.7342	Intermediate Similarity	NPC279434
0.734	Intermediate Similarity	NPC299100
0.734	Intermediate Similarity	NPC103527
0.7333	Intermediate Similarity	NPC472869
0.7333	Intermediate Similarity	NPC472479
0.7333	Intermediate Similarity	NPC472488
0.7333	Intermediate Similarity	NPC82979
0.7326	Intermediate Similarity	NPC152061
0.7326	Intermediate Similarity	NPC229204
0.7326	Intermediate Similarity	NPC19900
0.732	Intermediate Similarity	NPC470074
0.7317	Intermediate Similarity	NPC477792
0.7317	Intermediate Similarity	NPC23954
0.7312	Intermediate Similarity	NPC473675
0.7312	Intermediate Similarity	NPC131872
0.7312	Intermediate Similarity	NPC475806
0.7312	Intermediate Similarity	NPC476417
0.7303	Intermediate Similarity	NPC472265
0.7303	Intermediate Similarity	NPC302360
0.7303	Intermediate Similarity	NPC83702
0.7303	Intermediate Similarity	NPC164577
0.7303	Intermediate Similarity	NPC472865
0.7294	Intermediate Similarity	NPC476007
0.7294	Intermediate Similarity	NPC91594
0.7292	Intermediate Similarity	NPC320306

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 NPC92226 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1737
0.2-0.3	4128
0.3-0.4	2207
0.4-0.5	525
0.5-0.6	258
0.6-0.7	103
0.7-0.8	3
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
0.7647	Intermediate Similarity	NPD4695	Discontinued
0.7528	Intermediate Similarity	NPD4623	Approved
0.7528	Intermediate Similarity	NPD4519	Discontinued
0.7333	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4195	Approved
0.7273	Intermediate Similarity	NPD4223	Phase 3
0.7273	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD5690	Phase 2
0.7143	Intermediate Similarity	NPD3618	Phase 1
0.7111	Intermediate Similarity	NPD4197	Approved
0.7053	Intermediate Similarity	NPD4202	Approved
0.7033	Intermediate Similarity	NPD1696	Phase 3
0.7033	Intermediate Similarity	NPD5329	Approved
0.7	Intermediate Similarity	NPD5211	Phase 2
0.6957	Remote Similarity	NPD4690	Approved
0.6957	Remote Similarity	NPD4693	Phase 3
0.6957	Remote Similarity	NPD5280	Approved
0.6957	Remote Similarity	NPD4689	Approved
0.6957	Remote Similarity	NPD5205	Approved
0.6957	Remote Similarity	NPD4138	Approved
0.6957	Remote Similarity	NPD4688	Approved
0.6957	Remote Similarity	NPD4694	Approved
0.6947	Remote Similarity	NPD6079	Approved
0.6923	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD3133	Approved
0.6923	Remote Similarity	NPD3666	Approved
0.6915	Remote Similarity	NPD5328	Approved
0.6889	Remote Similarity	NPD3667	Approved
0.6882	Remote Similarity	NPD3573	Approved
0.6869	Remote Similarity	NPD4225	Approved
0.6863	Remote Similarity	NPD5141	Approved
0.6818	Remote Similarity	NPD3617	Approved
0.68	Remote Similarity	NPD5286	Approved
0.68	Remote Similarity	NPD7639	Approved
0.68	Remote Similarity	NPD5285	Approved
0.68	Remote Similarity	NPD7640	Approved
0.68	Remote Similarity	NPD4696	Approved
0.6774	Remote Similarity	NPD5279	Phase 3
0.6771	Remote Similarity	NPD5281	Approved
0.6771	Remote Similarity	NPD7515	Phase 2
0.6771	Remote Similarity	NPD5284	Approved
0.6768	Remote Similarity	NPD4755	Approved
0.6739	Remote Similarity	NPD4786	Approved
0.6737	Remote Similarity	NPD4753	Phase 2
0.6733	Remote Similarity	NPD5223	Approved
0.6707	Remote Similarity	NPD7331	Phase 2
0.6702	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD4096	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6634	Remote Similarity	NPD4700	Approved
0.6633	Remote Similarity	NPD7748	Approved
0.6632	Remote Similarity	NPD4518	Approved
0.6602	Remote Similarity	NPD5175	Approved
0.6602	Remote Similarity	NPD5174	Approved
0.66	Remote Similarity	NPD7902	Approved
0.66	Remote Similarity	NPD5173	Approved
0.6588	Remote Similarity	NPD4691	Approved
0.6585	Remote Similarity	NPD7341	Phase 2
0.6566	Remote Similarity	NPD5210	Approved
0.6566	Remote Similarity	NPD4629	Approved
0.6562	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6929	Approved
0.6552	Remote Similarity	NPD4785	Approved
0.6552	Remote Similarity	NPD4784	Approved
0.6542	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4243	Approved
0.65	Remote Similarity	NPD4697	Phase 3
0.6489	Remote Similarity	NPD1694	Approved
0.6484	Remote Similarity	NPD7525	Registered
0.6484	Remote Similarity	NPD7514	Phase 3
0.6484	Remote Similarity	NPD7332	Phase 2
0.6471	Remote Similarity	NPD4137	Phase 3
0.6452	Remote Similarity	NPD6695	Phase 3
0.6442	Remote Similarity	NPD4754	Approved
0.642	Remote Similarity	NPD368	Approved
0.6415	Remote Similarity	NPD5697	Approved
0.6413	Remote Similarity	NPD4692	Approved
0.6413	Remote Similarity	NPD4139	Approved
0.6408	Remote Similarity	NPD5344	Discontinued
0.6404	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5695	Phase 3
0.6395	Remote Similarity	NPD4747	Approved
0.6383	Remote Similarity	NPD3668	Phase 3
0.6374	Remote Similarity	NPD7645	Phase 2
0.6364	Remote Similarity	NPD4058	Approved
0.6364	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD6926	Approved
0.6364	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD5133	Approved
0.6364	Remote Similarity	NPD6924	Approved
0.6355	Remote Similarity	NPD4729	Approved
0.6355	Remote Similarity	NPD6881	Approved
0.6355	Remote Similarity	NPD6011	Approved
0.6355	Remote Similarity	NPD6899	Approved
0.6355	Remote Similarity	NPD4730	Approved
0.6355	Remote Similarity	NPD5128	Approved
0.6339	Remote Similarity	NPD7115	Discovery
0.6333	Remote Similarity	NPD6925	Approved
0.6333	Remote Similarity	NPD5776	Phase 2
0.6322	Remote Similarity	NPD5276	Approved
0.6321	Remote Similarity	NPD4768	Approved
0.6321	Remote Similarity	NPD7128	Approved
0.6321	Remote Similarity	NPD5739	Approved
0.6321	Remote Similarity	NPD6402	Approved
0.6321	Remote Similarity	NPD4767	Approved
0.6321	Remote Similarity	NPD6008	Approved
0.6321	Remote Similarity	NPD6675	Approved
0.6316	Remote Similarity	NPD6893	Approved
0.6311	Remote Similarity	NPD6404	Discontinued
0.6311	Remote Similarity	NPD6648	Approved
0.6304	Remote Similarity	NPD7509	Discontinued
0.6304	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6001	Approved
0.63	Remote Similarity	NPD5282	Discontinued
0.63	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7900	Approved
0.6296	Remote Similarity	NPD6013	Approved
0.6296	Remote Similarity	NPD6014	Approved
0.6296	Remote Similarity	NPD6012	Approved
0.6292	Remote Similarity	NPD7339	Approved
0.6292	Remote Similarity	NPD6942	Approved
0.6292	Remote Similarity	NPD4190	Phase 3
0.6292	Remote Similarity	NPD5275	Approved
0.6289	Remote Similarity	NPD5208	Approved
0.6277	Remote Similarity	NPD4788	Approved
0.6275	Remote Similarity	NPD6084	Phase 2
0.6275	Remote Similarity	NPD6083	Phase 2
0.6264	Remote Similarity	NPD7145	Approved
0.6264	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5693	Phase 1
0.6263	Remote Similarity	NPD7637	Suspended
0.6262	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD7146	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD7334	Approved
0.6239	Remote Similarity	NPD5249	Phase 3
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD5250	Approved
0.6239	Remote Similarity	NPD5135	Approved
0.6239	Remote Similarity	NPD5247	Approved
0.6239	Remote Similarity	NPD5169	Approved
0.6239	Remote Similarity	NPD6371	Approved
0.6239	Remote Similarity	NPD5251	Approved
0.6239	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5248	Approved
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.6238	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6898	Phase 1
0.6237	Remote Similarity	NPD6902	Approved
0.6224	Remote Similarity	NPD6904	Approved
0.6224	Remote Similarity	NPD6080	Approved
0.6224	Remote Similarity	NPD6673	Approved
0.6222	Remote Similarity	NPD6933	Approved
0.622	Remote Similarity	NPD4194	Approved
0.622	Remote Similarity	NPD4192	Approved
0.622	Remote Similarity	NPD4193	Approved
0.622	Remote Similarity	NPD4191	Approved
0.6214	Remote Similarity	NPD5290	Discontinued
0.6214	Remote Similarity	NPD5696	Approved
0.6204	Remote Similarity	NPD7320	Approved
0.6204	Remote Similarity	NPD6686	Approved
0.6195	Remote Similarity	NPD6009	Approved
0.619	Remote Similarity	NPD7632	Discontinued
0.619	Remote Similarity	NPD5091	Approved
0.6186	Remote Similarity	NPD7524	Approved
0.6186	Remote Similarity	NPD7750	Discontinued
0.6182	Remote Similarity	NPD5127	Approved
0.6182	Remote Similarity	NPD6649	Approved
0.6182	Remote Similarity	NPD5217	Approved
0.6182	Remote Similarity	NPD6847	Approved
0.6182	Remote Similarity	NPD6869	Approved
0.6182	Remote Similarity	NPD6650	Approved
0.6182	Remote Similarity	NPD8130	Phase 1
0.6182	Remote Similarity	NPD5215	Approved
0.6182	Remote Similarity	NPD5216	Approved
0.6182	Remote Similarity	NPD6617	Approved
0.618	Remote Similarity	NPD4687	Approved
0.618	Remote Similarity	NPD5733	Approved
0.6176	Remote Similarity	NPD7614	Phase 1
0.6162	Remote Similarity	NPD5692	Phase 3
0.6162	Remote Similarity	NPD5207	Approved
0.6154	Remote Similarity	NPD6932	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