NPASS Compound

Structure

NPC474387 OpenBabel07101718242D 28 30 0 0 1 0 0 0 0 0999 V2000 -2.6483 -2.3920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2956 -1.8567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0085 -0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 -1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 0.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 -0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 6 7 2 0 0 0 0 6 17 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 18 2 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 21 2 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 18 20 1 0 0 0 0 19 4 1 1 0 0 0 19 23 1 0 0 0 0 21 27 1 0 0 0 0 22 11 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 1 0 0 0 24 26 1 1 0 0 0 25 28 1 6 0 0 0 26 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.3
Volume:	439.617
LogP:	6.486
LogD:	5.941
LogS:	-5.982
# Rotatable Bonds:	6
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.566
Synthetic Accessibility Score:	4.202
Fsp3:	0.692
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.664
MDCK Permeability:	2.2034510038793087e-05
Pgp-inhibitor:	0.271
Pgp-substrate:	0.086
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	97.0902328491211%
Volume Distribution (VD):	2.0
Pgp-substrate:	1.9022884368896484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.337
CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.461
CYP2C19-substrate:	0.904
CYP2C9-inhibitor:	0.51
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.679
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.764
CYP3A4-substrate:	0.626

ADMET: Excretion

Clearance (CL):	2.96
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.197
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.204
Skin Sensitization:	0.721
Carcinogencity:	0.011
Eye Corrosion:	0.068
Eye Irritation:	0.475
Respiratory Toxicity:	0.325

Download Data

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

Natural Product: NPC474387

Natural Product ID:	NPC474387
*Common Name:**	Calicoferol H
IUPAC Name:	(1R,3aS,4S,5R,7aR)-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-1-[(E,2R)-5-methylhex-3-en-2-yl]-1,2,3,3a,4,5,6,7-octahydroinden-5-ol
Synonyms:	Calicoferol H
Standard InCHIKey:	YRVRPIWMDMUJBK-JTOPQAQZSA-N
Standard InCHI:	InChI=1S/C26H40O2/c1-17(2)6-7-19(4)23-12-13-24-22(25(28)14-15-26(23,24)5)11-9-20-16-21(27)10-8-18(20)3/h6-8,10,16-17,19,22-25,27-28H,9,11-15H2,1-5H3/b7-6+/t19-,22+,23-,24+,25-,26-/m1/s1
SMILES:	CC1=C(C=C(C=C1)O)CCC2C3CCC(C3(CCC2O)C)C(C)C=CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465816
PubChem CID:	21672158
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001272] Cresols [CHEMONTID:0001275] Para cresols

*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
NPO32639	muricella	Genus	Acanthogorgiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7595595]
NPO32639	muricella	Genus	Acanthogorgiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834177]

☑ 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
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	10.7	ug.mL-1	PMID[515228]
NPT545	Individual Protein	Phospholipase A2 group 1B	Homo sapiens	Inhibition	=	67.0	%	PMID[515228]

☑ 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 NPC474387 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	264
0.1-0.2	1292
0.2-0.3	2501
0.3-0.4	7515
0.4-0.5	11502
0.5-0.6	12560
0.6-0.7	5902
0.7-0.8	1031
0.8-0.85	82
0.85-0.9	34
0.9-0.95	7
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC257540
1.0	High Similarity	NPC154511
1.0	High Similarity	NPC247858
1.0	High Similarity	NPC474358
1.0	High Similarity	NPC137496
0.9643	High Similarity	NPC68339
0.9292	High Similarity	NPC164649
0.9292	High Similarity	NPC48342
0.9273	High Similarity	NPC228425
0.9217	High Similarity	NPC328504
0.9035	High Similarity	NPC477136
0.9027	High Similarity	NPC147179
0.9009	High Similarity	NPC322753
0.8974	High Similarity	NPC142198
0.8974	High Similarity	NPC77569
0.8947	High Similarity	NPC308311
0.8947	High Similarity	NPC308828
0.8947	High Similarity	NPC219112
0.8947	High Similarity	NPC477137
0.8947	High Similarity	NPC38893
0.8938	High Similarity	NPC268160
0.8917	High Similarity	NPC269598
0.8879	High Similarity	NPC473974
0.8879	High Similarity	NPC258366
0.8879	High Similarity	NPC31296
0.8879	High Similarity	NPC79933
0.886	High Similarity	NPC192948
0.886	High Similarity	NPC35797
0.8793	High Similarity	NPC469609
0.8793	High Similarity	NPC471671
0.8783	High Similarity	NPC469663
0.8783	High Similarity	NPC92
0.875	High Similarity	NPC13482
0.8739	High Similarity	NPC321402
0.8718	High Similarity	NPC469644
0.8707	High Similarity	NPC172219
0.8707	High Similarity	NPC304510
0.8696	High Similarity	NPC469719
0.8655	High Similarity	NPC475166
0.8644	High Similarity	NPC260832
0.8644	High Similarity	NPC135467
0.8644	High Similarity	NPC99734
0.8632	High Similarity	NPC154030
0.8596	High Similarity	NPC250323
0.8584	High Similarity	NPC141782
0.8584	High Similarity	NPC132720
0.8583	High Similarity	NPC297057
0.8571	High Similarity	NPC11554
0.8559	High Similarity	NPC151197
0.8545	High Similarity	NPC327811
0.8545	High Similarity	NPC254965
0.8537	High Similarity	NPC30491
0.8537	High Similarity	NPC262936
0.8534	High Similarity	NPC474486
0.8509	High Similarity	NPC176279
0.8509	High Similarity	NPC260323
0.8487	Intermediate Similarity	NPC190501
0.8487	Intermediate Similarity	NPC318552
0.8482	Intermediate Similarity	NPC320439
0.8482	Intermediate Similarity	NPC151477
0.8462	Intermediate Similarity	NPC471668
0.8448	Intermediate Similarity	NPC195922
0.844	Intermediate Similarity	NPC294741
0.844	Intermediate Similarity	NPC211885
0.8435	Intermediate Similarity	NPC62867
0.8435	Intermediate Similarity	NPC177962
0.843	Intermediate Similarity	NPC471794
0.8407	Intermediate Similarity	NPC64586
0.8407	Intermediate Similarity	NPC262365
0.8403	Intermediate Similarity	NPC323074
0.84	Intermediate Similarity	NPC288290
0.8378	Intermediate Similarity	NPC323810
0.8349	Intermediate Similarity	NPC78119
0.8349	Intermediate Similarity	NPC216468
0.8349	Intermediate Similarity	NPC132078
0.8349	Intermediate Similarity	NPC92730
0.8349	Intermediate Similarity	NPC51333
0.8348	Intermediate Similarity	NPC95716
0.8348	Intermediate Similarity	NPC77772
0.8348	Intermediate Similarity	NPC470770
0.8348	Intermediate Similarity	NPC266937
0.8346	Intermediate Similarity	NPC85595
0.8333	Intermediate Similarity	NPC477037
0.8333	Intermediate Similarity	NPC202986
0.8333	Intermediate Similarity	NPC318581
0.8333	Intermediate Similarity	NPC58865
0.8333	Intermediate Similarity	NPC325544
0.8305	Intermediate Similarity	NPC472862
0.8305	Intermediate Similarity	NPC141001
0.8304	Intermediate Similarity	NPC117115
0.8293	Intermediate Similarity	NPC181334
0.8279	Intermediate Similarity	NPC152946
0.8279	Intermediate Similarity	NPC478058
0.8276	Intermediate Similarity	NPC473521
0.8276	Intermediate Similarity	NPC46940
0.8273	Intermediate Similarity	NPC213730
0.8273	Intermediate Similarity	NPC225506
0.8261	Intermediate Similarity	NPC44732
0.8257	Intermediate Similarity	NPC225464
0.8257	Intermediate Similarity	NPC474073
0.825	Intermediate Similarity	NPC126002
0.825	Intermediate Similarity	NPC93071
0.824	Intermediate Similarity	NPC471077
0.8235	Intermediate Similarity	NPC16030
0.823	Intermediate Similarity	NPC310456
0.823	Intermediate Similarity	NPC155072
0.823	Intermediate Similarity	NPC21594
0.8226	Intermediate Similarity	NPC87985
0.8226	Intermediate Similarity	NPC76119
0.8226	Intermediate Similarity	NPC4286
0.8226	Intermediate Similarity	NPC124030
0.8217	Intermediate Similarity	NPC11266
0.8214	Intermediate Similarity	NPC475225
0.8211	Intermediate Similarity	NPC198014
0.8211	Intermediate Similarity	NPC471187
0.8205	Intermediate Similarity	NPC715
0.8198	Intermediate Similarity	NPC91461
0.8198	Intermediate Similarity	NPC471578
0.8198	Intermediate Similarity	NPC101025
0.8198	Intermediate Similarity	NPC7686
0.8198	Intermediate Similarity	NPC252105
0.8198	Intermediate Similarity	NPC40258
0.8197	Intermediate Similarity	NPC253627
0.819	Intermediate Similarity	NPC308689
0.819	Intermediate Similarity	NPC151537
0.8182	Intermediate Similarity	NPC122005
0.8182	Intermediate Similarity	NPC128723
0.8182	Intermediate Similarity	NPC252821
0.8174	Intermediate Similarity	NPC62258
0.8174	Intermediate Similarity	NPC55617
0.8165	Intermediate Similarity	NPC216520
0.8165	Intermediate Similarity	NPC292730
0.8165	Intermediate Similarity	NPC473388
0.8165	Intermediate Similarity	NPC132271
0.8165	Intermediate Similarity	NPC82664
0.8158	Intermediate Similarity	NPC472980
0.8158	Intermediate Similarity	NPC472979
0.8158	Intermediate Similarity	NPC27252
0.8151	Intermediate Similarity	NPC33900
0.8148	Intermediate Similarity	NPC27323
0.8148	Intermediate Similarity	NPC316301
0.8142	Intermediate Similarity	NPC243601
0.8142	Intermediate Similarity	NPC219286
0.8142	Intermediate Similarity	NPC233396
0.8142	Intermediate Similarity	NPC138942
0.8142	Intermediate Similarity	NPC471350
0.8142	Intermediate Similarity	NPC154899
0.8142	Intermediate Similarity	NPC99557
0.8136	Intermediate Similarity	NPC12656
0.8136	Intermediate Similarity	NPC471534
0.8136	Intermediate Similarity	NPC107240
0.8136	Intermediate Similarity	NPC120280
0.813	Intermediate Similarity	NPC71094
0.813	Intermediate Similarity	NPC11250
0.813	Intermediate Similarity	NPC121168
0.8125	Intermediate Similarity	NPC235762
0.8125	Intermediate Similarity	NPC471228
0.8125	Intermediate Similarity	NPC168829
0.812	Intermediate Similarity	NPC302371
0.8115	Intermediate Similarity	NPC259703
0.8115	Intermediate Similarity	NPC32322
0.8115	Intermediate Similarity	NPC241001
0.811	Intermediate Similarity	NPC30174
0.8103	Intermediate Similarity	NPC147634
0.8103	Intermediate Similarity	NPC226401
0.8103	Intermediate Similarity	NPC79793
0.8103	Intermediate Similarity	NPC296683
0.8103	Intermediate Similarity	NPC120982
0.8103	Intermediate Similarity	NPC174096
0.8099	Intermediate Similarity	NPC42657
0.8091	Intermediate Similarity	NPC32674
0.8091	Intermediate Similarity	NPC77492
0.8087	Intermediate Similarity	NPC306295
0.8087	Intermediate Similarity	NPC149455
0.8087	Intermediate Similarity	NPC64642
0.8087	Intermediate Similarity	NPC472982
0.8073	Intermediate Similarity	NPC32714
0.8073	Intermediate Similarity	NPC222146
0.8073	Intermediate Similarity	NPC274678
0.8073	Intermediate Similarity	NPC26244
0.807	Intermediate Similarity	NPC135464
0.807	Intermediate Similarity	NPC92623
0.807	Intermediate Similarity	NPC477814
0.807	Intermediate Similarity	NPC271274
0.8062	Intermediate Similarity	NPC321502
0.8056	Intermediate Similarity	NPC147284
0.8056	Intermediate Similarity	NPC55903
0.8056	Intermediate Similarity	NPC162314
0.8056	Intermediate Similarity	NPC138117
0.8056	Intermediate Similarity	NPC210497
0.8056	Intermediate Similarity	NPC3358
0.8056	Intermediate Similarity	NPC94139
0.8056	Intermediate Similarity	NPC325292
0.8056	Intermediate Similarity	NPC306884
0.8053	Intermediate Similarity	NPC56168
0.8053	Intermediate Similarity	NPC288411
0.8051	Intermediate Similarity	NPC176730
0.8051	Intermediate Similarity	NPC123175
0.8034	Intermediate Similarity	NPC179002
0.8034	Intermediate Similarity	NPC187583

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 NPC474387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	861
0.2-0.3	1218
0.3-0.4	2766
0.4-0.5	2247
0.5-0.6	1347
0.6-0.7	388
0.7-0.8	65
0.8-0.85	7
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9292	High Similarity	NPD3091	Approved
0.8974	High Similarity	NPD3092	Approved
0.8803	High Similarity	NPD3095	Discontinued
0.8678	High Similarity	NPD3094	Phase 2
0.8644	High Similarity	NPD4059	Approved
0.8537	High Similarity	NPD5736	Approved
0.8487	Intermediate Similarity	NPD2932	Approved
0.8487	Intermediate Similarity	NPD3019	Approved
0.8349	Intermediate Similarity	NPD3020	Approved
0.8268	Intermediate Similarity	NPD6663	Approved
0.8148	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD7635	Approved
0.8092	Intermediate Similarity	NPD7743	Approved
0.8092	Intermediate Similarity	NPD7742	Approved
0.8073	Intermediate Similarity	NPD2859	Approved
0.8073	Intermediate Similarity	NPD2860	Approved
0.8065	Intermediate Similarity	NPD5327	Phase 3
0.8062	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD3620	Phase 2
0.8017	Intermediate Similarity	NPD3021	Approved
0.8017	Intermediate Similarity	NPD3022	Approved
0.8016	Intermediate Similarity	NPD4624	Approved
0.8	Intermediate Similarity	NPD5735	Approved
0.7982	Intermediate Similarity	NPD2933	Approved
0.7982	Intermediate Similarity	NPD2934	Approved
0.7946	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6353	Approved
0.7923	Intermediate Similarity	NPD4140	Approved
0.7909	Intermediate Similarity	NPD1809	Phase 2
0.7903	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD288	Approved
0.7823	Intermediate Similarity	NPD3026	Approved
0.7823	Intermediate Similarity	NPD3023	Approved
0.7805	Intermediate Similarity	NPD3024	Approved
0.7805	Intermediate Similarity	NPD3025	Approved
0.7778	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD844	Approved
0.7742	Intermediate Similarity	NPD1751	Approved
0.7737	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD845	Approved
0.7721	Intermediate Similarity	NPD3638	Discontinued
0.7692	Intermediate Similarity	NPD2342	Discontinued
0.7674	Intermediate Similarity	NPD2861	Phase 2
0.7661	Intermediate Similarity	NPD4093	Discontinued
0.7581	Intermediate Similarity	NPD7741	Discontinued
0.7563	Intermediate Similarity	NPD1792	Phase 2
0.7563	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2194	Approved
0.7462	Intermediate Similarity	NPD2195	Approved
0.7459	Intermediate Similarity	NPD2234	Approved
0.7459	Intermediate Similarity	NPD2229	Approved
0.7459	Intermediate Similarity	NPD2228	Approved
0.7445	Intermediate Similarity	NPD5763	Approved
0.7445	Intermediate Similarity	NPD5762	Approved
0.7414	Intermediate Similarity	NPD940	Approved
0.7414	Intermediate Similarity	NPD846	Approved
0.7407	Intermediate Similarity	NPD4097	Suspended
0.7405	Intermediate Similarity	NPD3635	Approved
0.7405	Intermediate Similarity	NPD3636	Approved
0.7405	Intermediate Similarity	NPD3637	Approved
0.7388	Intermediate Similarity	NPD4060	Phase 1
0.7357	Intermediate Similarity	NPD8131	Suspended
0.7348	Intermediate Similarity	NPD2605	Approved
0.7348	Intermediate Similarity	NPD2606	Approved
0.7339	Intermediate Similarity	NPD7157	Approved
0.7328	Intermediate Similarity	NPD1242	Phase 1
0.7324	Intermediate Similarity	NPD3645	Discontinued
0.7323	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2286	Discontinued
0.7323	Intermediate Similarity	NPD4626	Approved
0.7323	Intermediate Similarity	NPD4589	Approved
0.7315	Intermediate Similarity	NPD111	Approved
0.7311	Intermediate Similarity	NPD1444	Approved
0.7311	Intermediate Similarity	NPD1445	Approved
0.7293	Intermediate Similarity	NPD5155	Approved
0.7293	Intermediate Similarity	NPD5156	Approved
0.728	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2157	Approved
0.7252	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3594	Approved
0.7218	Intermediate Similarity	NPD3595	Approved
0.7206	Intermediate Similarity	NPD3657	Discovery
0.72	Intermediate Similarity	NPD6671	Approved
0.7185	Intermediate Similarity	NPD8032	Phase 2
0.7177	Intermediate Similarity	NPD5283	Phase 1
0.7177	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6696	Suspended
0.7165	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5303	Approved
0.7165	Intermediate Similarity	NPD5304	Approved
0.7154	Intermediate Similarity	NPD2232	Approved
0.7154	Intermediate Similarity	NPD2233	Approved
0.7154	Intermediate Similarity	NPD2230	Approved
0.7153	Intermediate Similarity	NPD6273	Approved
0.7132	Intermediate Similarity	NPD2238	Phase 2
0.7109	Intermediate Similarity	NPD1357	Approved
0.7109	Intermediate Similarity	NPD5691	Approved
0.7103	Intermediate Similarity	NPD5699	Approved
0.7099	Intermediate Similarity	NPD4659	Approved
0.7049	Intermediate Similarity	NPD2684	Approved
0.7045	Intermediate Similarity	NPD1283	Approved
0.7042	Intermediate Similarity	NPD8166	Discontinued
0.7037	Intermediate Similarity	NPD3027	Phase 3
0.7034	Intermediate Similarity	NPD3028	Approved
0.7031	Intermediate Similarity	NPD7330	Discontinued
0.7016	Intermediate Similarity	NPD228	Approved
0.7014	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7041	Phase 2
0.6992	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4103	Phase 2
0.6985	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD9618	Approved
0.6984	Remote Similarity	NPD497	Approved
0.6984	Remote Similarity	NPD1793	Approved
0.6984	Remote Similarity	NPD1791	Approved
0.6984	Remote Similarity	NPD9614	Approved
0.6984	Remote Similarity	NPD2629	Approved
0.6977	Remote Similarity	NPD1651	Approved
0.6977	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1669	Approved
0.6966	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4908	Phase 1
0.696	Remote Similarity	NPD7843	Approved
0.6957	Remote Similarity	NPD6355	Discontinued
0.695	Remote Similarity	NPD4726	Approved
0.695	Remote Similarity	NPD4721	Approved
0.695	Remote Similarity	NPD4725	Approved
0.6947	Remote Similarity	NPD1201	Approved
0.6947	Remote Similarity	NPD1610	Phase 2
0.694	Remote Similarity	NPD6584	Phase 3
0.6934	Remote Similarity	NPD6407	Approved
0.6934	Remote Similarity	NPD6405	Approved
0.6923	Remote Similarity	NPD2668	Approved
0.6923	Remote Similarity	NPD2667	Approved
0.6917	Remote Similarity	NPD8651	Approved
0.6917	Remote Similarity	NPD1876	Approved
0.6912	Remote Similarity	NPD4625	Phase 3
0.6908	Remote Similarity	NPD7833	Phase 2
0.6908	Remote Similarity	NPD7831	Phase 2
0.6908	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD495	Approved
0.6905	Remote Similarity	NPD496	Approved
0.6905	Remote Similarity	NPD498	Approved
0.6901	Remote Similarity	NPD7037	Approved
0.6894	Remote Similarity	NPD2231	Phase 2
0.6894	Remote Similarity	NPD2561	Approved
0.6894	Remote Similarity	NPD2562	Approved
0.6894	Remote Similarity	NPD2235	Phase 2
0.6875	Remote Similarity	NPD7340	Approved
0.687	Remote Similarity	NPD3143	Discontinued
0.6861	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9615	Approved
0.6822	Remote Similarity	NPD856	Approved
0.6822	Remote Similarity	NPD9616	Approved
0.6822	Remote Similarity	NPD9613	Approved
0.6822	Remote Similarity	NPD16	Approved
0.6818	Remote Similarity	NPD1281	Approved
0.6809	Remote Similarity	NPD1753	Discontinued
0.6806	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3892	Phase 2
0.6806	Remote Similarity	NPD4110	Phase 3
0.6797	Remote Similarity	NPD709	Approved
0.6794	Remote Similarity	NPD9384	Approved
0.6794	Remote Similarity	NPD9381	Approved
0.6788	Remote Similarity	NPD7095	Approved
0.6786	Remote Similarity	NPD6653	Approved
0.6777	Remote Similarity	NPD9500	Approved
0.6774	Remote Similarity	NPD8127	Discontinued
0.6769	Remote Similarity	NPD316	Approved
0.6767	Remote Similarity	NPD3070	Discontinued
0.6765	Remote Similarity	NPD1712	Approved
0.6765	Remote Similarity	NPD4208	Discontinued
0.6763	Remote Similarity	NPD6346	Approved
0.6748	Remote Similarity	NPD968	Approved
0.6744	Remote Similarity	NPD7636	Approved
0.6744	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD1135	Approved
0.6741	Remote Similarity	NPD1131	Approved
0.6741	Remote Similarity	NPD1133	Approved
0.6741	Remote Similarity	NPD1134	Approved
0.6741	Remote Similarity	NPD1129	Approved
0.6741	Remote Similarity	NPD1470	Approved
0.6721	Remote Similarity	NPD9610	Approved
0.6721	Remote Similarity	NPD9608	Approved
0.672	Remote Similarity	NPD5451	Approved
0.6719	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5585	Approved
0.6716	Remote Similarity	NPD6582	Phase 2
0.6716	Remote Similarity	NPD9622	Approved
0.6716	Remote Similarity	NPD6583	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