NPASS Compound

Structure

NPC471671 OpenBabel07101718232D 22 24 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 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 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 0.8660 -1.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 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 1.7321 -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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 13 16 2 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.767
LogD:	4.076
LogS:	-4.094
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.763
Synthetic Accessibility Score:	3.808
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.715
MDCK Permeability:	1.645121483306866e-05
Pgp-inhibitor:	0.925
Pgp-substrate:	0.134
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.468
Plasma Protein Binding (PPB):	95.01065826416016%
Volume Distribution (VD):	2.996
Pgp-substrate:	6.915027618408203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.172
CYP1A2-substrate:	0.877
CYP2C19-inhibitor:	0.222
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.207
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.313
CYP2D6-substrate:	0.721
CYP3A4-inhibitor:	0.25
CYP3A4-substrate:	0.646

ADMET: Excretion

Clearance (CL):	10.114
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.5
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.817
Carcinogencity:	0.097
Eye Corrosion:	0.004
Eye Irritation:	0.894
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC471671

Natural Product ID:	NPC471671
*Common Name:**	7-Hydroxyferruginol
IUPAC Name:	(4bS,8aS)-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthrene-3,10-diol
Synonyms:
Standard InCHIKey:	GGSVAHYPLRMGPQ-AQCCAAQSSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-12(2)13-9-14-15(10-16(13)21)20(5)8-6-7-19(3,4)18(20)11-17(14)22/h9-10,12,17-18,21-22H,6-8,11H2,1-5H3/t17?,18-,20+/m0/s1
SMILES:	CC(C)C1=C(C=C2C(=C1)C(CC3C2(CCCC3(C)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3093125
PubChem CID:	23900078
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
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24210499]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	whole plants	east Texas, USA	2009-2011	PMID[24210499]
NPO18892	Salvinia molesta	Species	Salviniaceae	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
GI50	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	GI50	=	70490.0	nM	PMID[477055]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	75190.0	nM	PMID[477055]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	85610.0	nM	PMID[477055]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	75110.0	nM	PMID[477055]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	74730.0	nM	PMID[477055]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	78240.0	nM	PMID[477055]

☑ 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 NPC471671 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	295
0.1-0.2	1426
0.2-0.3	2999
0.3-0.4	8606
0.4-0.5	10729
0.5-0.6	9349
0.6-0.7	7276
0.7-0.8	1732
0.8-0.85	176
0.85-0.9	70
0.9-0.95	21
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.991	High Similarity	NPC469644
0.9909	High Similarity	NPC172219
0.9909	High Similarity	NPC304510
0.9818	High Similarity	NPC38893
0.9818	High Similarity	NPC308311
0.9818	High Similarity	NPC477137
0.9727	High Similarity	NPC192948
0.9727	High Similarity	NPC35797
0.9643	High Similarity	NPC154030
0.9643	High Similarity	NPC469609
0.964	High Similarity	NPC219112
0.9554	High Similarity	NPC477136
0.955	High Similarity	NPC147179
0.9464	High Similarity	NPC92
0.9464	High Similarity	NPC469663
0.9464	High Similarity	NPC308828
0.9459	High Similarity	NPC268160
0.9364	High Similarity	NPC176279
0.9364	High Similarity	NPC260323
0.9231	High Similarity	NPC471794
0.9224	High Similarity	NPC328504
0.9167	High Similarity	NPC471077
0.9123	High Similarity	NPC471668
0.9115	High Similarity	NPC195922
0.9107	High Similarity	NPC250323
0.9107	High Similarity	NPC228425
0.9099	High Similarity	NPC132720
0.9099	High Similarity	NPC141782
0.9083	High Similarity	NPC325294
0.9083	High Similarity	NPC321822
0.9076	High Similarity	NPC181334
0.9068	High Similarity	NPC71094
0.9018	High Similarity	NPC151537
0.9	High Similarity	NPC124030
0.9	High Similarity	NPC87985
0.9	High Similarity	NPC151477
0.8992	High Similarity	NPC471187
0.8974	High Similarity	NPC135467
0.8974	High Similarity	NPC260832
0.8966	High Similarity	NPC48342
0.8966	High Similarity	NPC164649
0.8938	High Similarity	NPC46940
0.8929	High Similarity	NPC13482
0.8926	High Similarity	NPC43000
0.8926	High Similarity	NPC100414
0.8919	High Similarity	NPC64642
0.8919	High Similarity	NPC472982
0.8919	High Similarity	NPC149455
0.8908	High Similarity	NPC11250
0.8889	High Similarity	NPC93071
0.8889	High Similarity	NPC126002
0.886	High Similarity	NPC715
0.8852	High Similarity	NPC108164
0.8852	High Similarity	NPC186889
0.885	High Similarity	NPC95716
0.8824	High Similarity	NPC77569
0.8824	High Similarity	NPC142198
0.8818	High Similarity	NPC117115
0.8814	High Similarity	NPC68339
0.8803	High Similarity	NPC206
0.8793	High Similarity	NPC474358
0.8793	High Similarity	NPC137496
0.8793	High Similarity	NPC474387
0.8793	High Similarity	NPC247858
0.8793	High Similarity	NPC154511
0.8793	High Similarity	NPC257540
0.8793	High Similarity	NPC141001
0.8783	High Similarity	NPC471534
0.875	High Similarity	NPC152946
0.875	High Similarity	NPC11554
0.8739	High Similarity	NPC21594
0.8729	High Similarity	NPC151197
0.872	High Similarity	NPC312341
0.8718	High Similarity	NPC16030
0.8707	High Similarity	NPC469719
0.8699	High Similarity	NPC476536
0.8689	High Similarity	NPC4286
0.8689	High Similarity	NPC137750
0.8689	High Similarity	NPC76119
0.8684	High Similarity	NPC77772
0.8684	High Similarity	NPC322753
0.8678	High Similarity	NPC198014
0.8673	High Similarity	NPC58865
0.8667	High Similarity	NPC475166
0.8667	High Similarity	NPC249340
0.8667	High Similarity	NPC253627
0.8667	High Similarity	NPC162935
0.8661	High Similarity	NPC472979
0.8661	High Similarity	NPC27252
0.8651	High Similarity	NPC321086
0.8649	High Similarity	NPC243601
0.864	High Similarity	NPC196193
0.8609	High Similarity	NPC473521
0.8595	High Similarity	NPC321402
0.8595	High Similarity	NPC478058
0.8583	High Similarity	NPC259703
0.8583	High Similarity	NPC32322
0.8583	High Similarity	NPC227719
0.8571	High Similarity	NPC476847
0.8547	High Similarity	NPC84999
0.8547	High Similarity	NPC246760
0.8534	High Similarity	NPC317869
0.8534	High Similarity	NPC263753
0.8534	High Similarity	NPC319803
0.8522	High Similarity	NPC469912
0.8522	High Similarity	NPC470770
0.8522	High Similarity	NPC266937
0.8512	High Similarity	NPC154696
0.8509	High Similarity	NPC314187
0.8504	High Similarity	NPC59239
0.8504	High Similarity	NPC165612
0.8496	Intermediate Similarity	NPC472980
0.8492	Intermediate Similarity	NPC99795
0.8482	Intermediate Similarity	NPC219286
0.8482	Intermediate Similarity	NPC99557
0.8468	Intermediate Similarity	NPC470724
0.8462	Intermediate Similarity	NPC12656
0.8462	Intermediate Similarity	NPC107240
0.8462	Intermediate Similarity	NPC249270
0.8455	Intermediate Similarity	NPC211885
0.8448	Intermediate Similarity	NPC177962
0.8448	Intermediate Similarity	NPC302371
0.8448	Intermediate Similarity	NPC471179
0.8448	Intermediate Similarity	NPC62867
0.8443	Intermediate Similarity	NPC121168
0.8443	Intermediate Similarity	NPC176208
0.8438	Intermediate Similarity	NPC78307
0.8438	Intermediate Similarity	NPC49742
0.8435	Intermediate Similarity	NPC224870
0.843	Intermediate Similarity	NPC241001
0.8425	Intermediate Similarity	NPC471851
0.8425	Intermediate Similarity	NPC78575
0.8421	Intermediate Similarity	NPC262365
0.8417	Intermediate Similarity	NPC176893
0.8417	Intermediate Similarity	NPC323074
0.8407	Intermediate Similarity	NPC271274
0.8403	Intermediate Similarity	NPC299180
0.8393	Intermediate Similarity	NPC475225
0.839	Intermediate Similarity	NPC474486
0.8387	Intermediate Similarity	NPC470726
0.8385	Intermediate Similarity	NPC68292
0.8376	Intermediate Similarity	NPC117846
0.8376	Intermediate Similarity	NPC322239
0.8359	Intermediate Similarity	NPC85595
0.8347	Intermediate Similarity	NPC478121
0.8347	Intermediate Similarity	NPC325544
0.8347	Intermediate Similarity	NPC477037
0.8347	Intermediate Similarity	NPC318581
0.8333	Intermediate Similarity	NPC223912
0.8333	Intermediate Similarity	NPC320439
0.8333	Intermediate Similarity	NPC9592
0.8333	Intermediate Similarity	NPC48781
0.832	Intermediate Similarity	NPC71610
0.8319	Intermediate Similarity	NPC471350
0.8319	Intermediate Similarity	NPC472862
0.8306	Intermediate Similarity	NPC224342
0.8305	Intermediate Similarity	NPC473137
0.8304	Intermediate Similarity	NPC471228
0.8304	Intermediate Similarity	NPC235762
0.8304	Intermediate Similarity	NPC19856
0.8293	Intermediate Similarity	NPC297057
0.8288	Intermediate Similarity	NPC225506
0.8276	Intermediate Similarity	NPC296683
0.8276	Intermediate Similarity	NPC44732
0.8264	Intermediate Similarity	NPC42657
0.8254	Intermediate Similarity	NPC30491
0.8254	Intermediate Similarity	NPC262936
0.8254	Intermediate Similarity	NPC176130
0.8254	Intermediate Similarity	NPC78364
0.8254	Intermediate Similarity	NPC84672
0.8254	Intermediate Similarity	NPC69424
0.825	Intermediate Similarity	NPC320864
0.8231	Intermediate Similarity	NPC202225
0.823	Intermediate Similarity	NPC238696
0.823	Intermediate Similarity	NPC272029
0.8214	Intermediate Similarity	NPC252105
0.8211	Intermediate Similarity	NPC474115
0.8209	Intermediate Similarity	NPC272907
0.8209	Intermediate Similarity	NPC2681
0.8205	Intermediate Similarity	NPC224527
0.8205	Intermediate Similarity	NPC165770
0.8205	Intermediate Similarity	NPC225679
0.8205	Intermediate Similarity	NPC308689
0.8205	Intermediate Similarity	NPC476632
0.8205	Intermediate Similarity	NPC4493
0.8203	Intermediate Similarity	NPC470727
0.8203	Intermediate Similarity	NPC472793
0.8203	Intermediate Similarity	NPC249425
0.8198	Intermediate Similarity	NPC128723
0.8198	Intermediate Similarity	NPC33675
0.8198	Intermediate Similarity	NPC252821
0.8198	Intermediate Similarity	NPC299762
0.8198	Intermediate Similarity	NPC122005
0.8197	Intermediate Similarity	NPC318552
0.8197	Intermediate Similarity	NPC282255
0.8197	Intermediate Similarity	NPC99734
0.8197	Intermediate Similarity	NPC3239
0.8197	Intermediate Similarity	NPC190501
0.8197	Intermediate Similarity	NPC103916
0.8197	Intermediate Similarity	NPC223451

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 NPC471671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	875
0.2-0.3	1423
0.3-0.4	2864
0.4-0.5	1967
0.5-0.6	1214
0.6-0.7	421
0.7-0.8	94
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8966	High Similarity	NPD3091	Approved
0.8824	High Similarity	NPD3092	Approved
0.8537	High Similarity	NPD3094	Phase 2
0.85	High Similarity	NPD3095	Discontinued
0.8333	Intermediate Similarity	NPD2342	Discontinued
0.8291	Intermediate Similarity	NPD7635	Approved
0.8197	Intermediate Similarity	NPD3019	Approved
0.8197	Intermediate Similarity	NPD4059	Approved
0.819	Intermediate Similarity	NPD4750	Phase 3
0.811	Intermediate Similarity	NPD5736	Approved
0.8091	Intermediate Similarity	NPD1809	Phase 2
0.8049	Intermediate Similarity	NPD2932	Approved
0.8036	Intermediate Similarity	NPD3020	Approved
0.8018	Intermediate Similarity	NPD288	Approved
0.7939	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3620	Phase 2
0.7928	Intermediate Similarity	NPD844	Approved
0.7891	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD6663	Approved
0.7838	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD4097	Suspended
0.7807	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD2860	Approved
0.7768	Intermediate Similarity	NPD2859	Approved
0.776	Intermediate Similarity	NPD2286	Discontinued
0.775	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD845	Approved
0.7744	Intermediate Similarity	NPD5735	Approved
0.7731	Intermediate Similarity	NPD3021	Approved
0.7731	Intermediate Similarity	NPD3022	Approved
0.7704	Intermediate Similarity	NPD7743	Approved
0.7704	Intermediate Similarity	NPD7742	Approved
0.768	Intermediate Similarity	NPD4093	Discontinued
0.7679	Intermediate Similarity	NPD2933	Approved
0.7679	Intermediate Similarity	NPD2934	Approved
0.7672	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4140	Approved
0.7656	Intermediate Similarity	NPD5327	Phase 3
0.7638	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4626	Approved
0.7619	Intermediate Similarity	NPD1751	Approved
0.7615	Intermediate Similarity	NPD4624	Approved
0.7597	Intermediate Similarity	NPD6696	Suspended
0.7586	Intermediate Similarity	NPD846	Approved
0.7586	Intermediate Similarity	NPD940	Approved
0.7576	Intermediate Similarity	NPD4625	Phase 3
0.7559	Intermediate Similarity	NPD3023	Approved
0.7559	Intermediate Similarity	NPD3026	Approved
0.7557	Intermediate Similarity	NPD2861	Phase 2
0.754	Intermediate Similarity	NPD3025	Approved
0.754	Intermediate Similarity	NPD3024	Approved
0.7519	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2606	Approved
0.75	Intermediate Similarity	NPD2605	Approved
0.75	Intermediate Similarity	NPD1201	Approved
0.7482	Intermediate Similarity	NPD3638	Discontinued
0.7482	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5156	Approved
0.7444	Intermediate Similarity	NPD5155	Approved
0.744	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6353	Approved
0.7424	Intermediate Similarity	NPD3637	Approved
0.7424	Intermediate Similarity	NPD3635	Approved
0.7424	Intermediate Similarity	NPD3636	Approved
0.7407	Intermediate Similarity	NPD4060	Phase 1
0.7405	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD5691	Approved
0.7385	Intermediate Similarity	NPD4749	Approved
0.7376	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD3594	Approved
0.7368	Intermediate Similarity	NPD3595	Approved
0.735	Intermediate Similarity	NPD1242	Phase 1
0.7348	Intermediate Similarity	NPD2195	Approved
0.7348	Intermediate Similarity	NPD2194	Approved
0.7344	Intermediate Similarity	NPD4589	Approved
0.7343	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4725	Approved
0.7338	Intermediate Similarity	NPD4726	Approved
0.7338	Intermediate Similarity	NPD4721	Approved
0.7323	Intermediate Similarity	NPD7741	Discontinued
0.7319	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1792	Phase 2
0.728	Intermediate Similarity	NPD497	Approved
0.7273	Intermediate Similarity	NPD1470	Approved
0.7266	Intermediate Similarity	NPD5405	Approved
0.7266	Intermediate Similarity	NPD5406	Approved
0.7266	Intermediate Similarity	NPD5404	Approved
0.7266	Intermediate Similarity	NPD5408	Approved
0.7252	Intermediate Similarity	NPD4659	Approved
0.7234	Intermediate Similarity	NPD6674	Discontinued
0.7231	Intermediate Similarity	NPD1610	Phase 2
0.7222	Intermediate Similarity	NPD3645	Discontinued
0.72	Intermediate Similarity	NPD2228	Approved
0.72	Intermediate Similarity	NPD2234	Approved
0.72	Intermediate Similarity	NPD495	Approved
0.72	Intermediate Similarity	NPD2229	Approved
0.72	Intermediate Similarity	NPD498	Approved
0.72	Intermediate Similarity	NPD496	Approved
0.7197	Intermediate Similarity	NPD8651	Approved
0.7197	Intermediate Similarity	NPD1283	Approved
0.7188	Intermediate Similarity	NPD5304	Approved
0.7188	Intermediate Similarity	NPD5303	Approved
0.7183	Intermediate Similarity	NPD7003	Approved
0.7165	Intermediate Similarity	NPD7340	Approved
0.7153	Intermediate Similarity	NPD7390	Discontinued
0.7153	Intermediate Similarity	NPD2238	Phase 2
0.7153	Intermediate Similarity	NPD7041	Phase 2
0.7153	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4103	Phase 2
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7132	Intermediate Similarity	NPD1651	Approved
0.7101	Intermediate Similarity	NPD3657	Discovery
0.7092	Intermediate Similarity	NPD5763	Approved
0.7092	Intermediate Similarity	NPD5762	Approved
0.7092	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6407	Approved
0.708	Intermediate Similarity	NPD6405	Approved
0.7063	Intermediate Similarity	NPD1398	Phase 1
0.7063	Intermediate Similarity	NPD8166	Discontinued
0.7059	Intermediate Similarity	NPD3027	Phase 3
0.7054	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7330	Discontinued
0.7049	Intermediate Similarity	NPD1444	Approved
0.7049	Intermediate Similarity	NPD1445	Approved
0.7027	Intermediate Similarity	NPD111	Approved
0.7016	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1134	Approved
0.7015	Intermediate Similarity	NPD1131	Approved
0.7015	Intermediate Similarity	NPD1135	Approved
0.7015	Intermediate Similarity	NPD1129	Approved
0.7015	Intermediate Similarity	NPD1133	Approved
0.7	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1281	Approved
0.6963	Remote Similarity	NPD6584	Phase 3
0.6953	Remote Similarity	NPD7157	Approved
0.6953	Remote Similarity	NPD6671	Approved
0.695	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5126	Approved
0.6947	Remote Similarity	NPD5125	Phase 3
0.6939	Remote Similarity	NPD6273	Approved
0.6929	Remote Similarity	NPD5283	Phase 1
0.6923	Remote Similarity	NPD1548	Phase 1
0.6923	Remote Similarity	NPD7037	Approved
0.6917	Remote Similarity	NPD2562	Approved
0.6917	Remote Similarity	NPD2230	Approved
0.6917	Remote Similarity	NPD2561	Approved
0.6917	Remote Similarity	NPD2233	Approved
0.6917	Remote Similarity	NPD2232	Approved
0.6912	Remote Similarity	NPD4208	Discontinued
0.6906	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1613	Approved
0.6897	Remote Similarity	NPD8131	Suspended
0.6894	Remote Similarity	NPD3143	Discontinued
0.6892	Remote Similarity	NPD5699	Approved
0.6887	Remote Similarity	NPD37	Approved
0.6884	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3552	Approved
0.6879	Remote Similarity	NPD3554	Approved
0.6879	Remote Similarity	NPD3555	Approved
0.6879	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3553	Approved
0.6875	Remote Similarity	NPD5951	Approved
0.6875	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1669	Approved
0.6846	Remote Similarity	NPD856	Approved
0.6846	Remote Similarity	NPD16	Approved
0.6835	Remote Similarity	NPD8032	Phase 2
0.6828	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7725	Approved
0.6818	Remote Similarity	NPD9384	Approved
0.6818	Remote Similarity	NPD1778	Approved
0.6818	Remote Similarity	NPD9381	Approved
0.6809	Remote Similarity	NPD2157	Approved
0.6809	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2421	Approved
0.6803	Remote Similarity	NPD2420	Approved
0.6803	Remote Similarity	NPD9500	Approved
0.68	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2684	Approved
0.6791	Remote Similarity	NPD3070	Discontinued
0.6786	Remote Similarity	NPD3109	Approved
0.6786	Remote Similarity	NPD2979	Phase 3
0.6786	Remote Similarity	NPD3110	Approved
0.6777	Remote Similarity	NPD3028	Approved
0.6774	Remote Similarity	NPD5709	Phase 3
0.6772	Remote Similarity	NPD2489	Approved
0.6772	Remote Similarity	NPD27	Approved
0.6772	Remote Similarity	NPD228	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