NPASS Compound

Structure

CID319803 OpenBabel06191716152D 25 26 0 0 1 0 0 0 0 0999 V2000 4.1698 5.2963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 5.2963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -2.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5019 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 2.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 2.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 3.3704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3358 4.8148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8340 -0.4815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3358 3.8519 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1698 3.3704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 -1.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 2 0 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 21 2 0 0 0 0 13 19 1 0 0 0 0 17 16 1 6 0 0 0 17 18 1 0 0 0 0 18 22 1 1 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.22
Volume:	382.507
LogP:	4.759
LogD:	3.717
LogS:	-3.438
# Rotatable Bonds:	6
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	4.146
Fsp3:	0.455
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:	-4.756
MDCK Permeability:	1.2890182006231043e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.516
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	95.93976593017578%
Volume Distribution (VD):	1.363
Pgp-substrate:	1.5201048851013184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.531
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.287
CYP2C19-substrate:	0.76
CYP2C9-inhibitor:	0.659
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.447
CYP2D6-substrate:	0.753
CYP3A4-inhibitor:	0.443
CYP3A4-substrate:	0.436

ADMET: Excretion

Clearance (CL):	6.746
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.551
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.437
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.339
Carcinogencity:	0.193
Eye Corrosion:	0.003
Eye Irritation:	0.189
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC319803

Natural Product ID:	NPC319803
*Common Name:**	Ferruginene C
IUPAC Name:	2-[(1R,6R)-6-(5-hydroxy-6-methylhepta-1,6-dien-2-yl)-3-methylcyclohex-2-en-1-yl]-5-methylbenzene-1,3-diol
Synonyms:	Ferruginene C
Standard InCHIKey:	LQECQNLKIZLVSL-PAMZHZACSA-N
Standard InCHI:	InChI=1S/C22H30O3/c1-13(2)19(23)9-7-16(5)17-8-6-14(3)10-18(17)22-20(24)11-15(4)12-21(22)25/h10-12,17-19,23-25H,1,5-9H2,2-4H3/t17-,18+,19?/m0/s1
SMILES:	CC(=C)C(CCC(=C)[C@@H]1CCC(=C[C@H]1c1c(O)cc(cc1O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1775033
PubChem CID:	52951888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	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
IC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	13700.0	nM	PMID[469011]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20000.0	nM	PMID[469011]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	20000.0	nM	PMID[469011]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[469011]

☑ 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 NPC319803 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	286
0.1-0.2	1301
0.2-0.3	3478
0.3-0.4	11553
0.4-0.5	8581
0.5-0.6	8704
0.6-0.7	6789
0.7-0.8	1754
0.8-0.85	149
0.85-0.9	73
0.9-0.95	22
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9619	High Similarity	NPC299568
0.9619	High Similarity	NPC186385
0.9369	High Similarity	NPC9592
0.9369	High Similarity	NPC48781
0.9259	High Similarity	NPC224527
0.9238	High Similarity	NPC37802
0.9174	High Similarity	NPC473521
0.9151	High Similarity	NPC12640
0.9151	High Similarity	NPC201662
0.9151	High Similarity	NPC99836
0.9143	High Similarity	NPC244513
0.9143	High Similarity	NPC218879
0.9143	High Similarity	NPC227458
0.9091	High Similarity	NPC261343
0.9091	High Similarity	NPC23804
0.9074	High Similarity	NPC33728
0.9074	High Similarity	NPC19808
0.9065	High Similarity	NPC61033
0.9065	High Similarity	NPC305603
0.9065	High Similarity	NPC204901
0.9065	High Similarity	NPC232523
0.9065	High Similarity	NPC158253
0.8981	High Similarity	NPC174981
0.8929	High Similarity	NPC246760
0.8929	High Similarity	NPC84999
0.8889	High Similarity	NPC66834
0.8829	High Similarity	NPC166995
0.8814	High Similarity	NPC139774
0.8814	High Similarity	NPC174729
0.8785	High Similarity	NPC475225
0.8774	High Similarity	NPC294186
0.8774	High Similarity	NPC11280
0.8774	High Similarity	NPC137415
0.8774	High Similarity	NPC147310
0.8774	High Similarity	NPC24407
0.8774	High Similarity	NPC192032
0.8774	High Similarity	NPC166313
0.875	High Similarity	NPC117846
0.875	High Similarity	NPC263753
0.8704	High Similarity	NPC471350
0.8696	High Similarity	NPC154030
0.8696	High Similarity	NPC206
0.8692	High Similarity	NPC249828
0.8692	High Similarity	NPC242342
0.8692	High Similarity	NPC71002
0.8692	High Similarity	NPC146798
0.8692	High Similarity	NPC53051
0.8692	High Similarity	NPC471228
0.8692	High Similarity	NPC313030
0.8692	High Similarity	NPC168303
0.8692	High Similarity	NPC222522
0.8692	High Similarity	NPC85479
0.8692	High Similarity	NPC24404
0.8692	High Similarity	NPC302219
0.8692	High Similarity	NPC106396
0.8692	High Similarity	NPC235762
0.8692	High Similarity	NPC94351
0.8679	High Similarity	NPC10588
0.8679	High Similarity	NPC166761
0.8678	High Similarity	NPC38604
0.8678	High Similarity	NPC211179
0.8667	High Similarity	NPC111723
0.8667	High Similarity	NPC237517
0.8667	High Similarity	NPC91204
0.8661	High Similarity	NPC228452
0.8649	High Similarity	NPC475018
0.8649	High Similarity	NPC224870
0.8649	High Similarity	NPC132720
0.8611	High Similarity	NPC102216
0.8611	High Similarity	NPC241891
0.8609	High Similarity	NPC320864
0.8607	High Similarity	NPC472795
0.8607	High Similarity	NPC472796
0.8598	High Similarity	NPC72947
0.8598	High Similarity	NPC284011
0.8595	High Similarity	NPC66331
0.8595	High Similarity	NPC32715
0.8595	High Similarity	NPC98200
0.8571	High Similarity	NPC476632
0.8571	High Similarity	NPC54373
0.8571	High Similarity	NPC165770
0.8571	High Similarity	NPC4493
0.8571	High Similarity	NPC225679
0.8547	High Similarity	NPC223451
0.8534	High Similarity	NPC190514
0.8534	High Similarity	NPC471671
0.8532	High Similarity	NPC134829
0.8532	High Similarity	NPC246056
0.8522	High Similarity	NPC115808
0.8509	High Similarity	NPC107240
0.8505	High Similarity	NPC72729
0.8505	High Similarity	NPC174911
0.8496	Intermediate Similarity	NPC43525
0.8496	Intermediate Similarity	NPC302371
0.8491	Intermediate Similarity	NPC79241
0.8491	Intermediate Similarity	NPC6597
0.8487	Intermediate Similarity	NPC77789
0.8487	Intermediate Similarity	NPC18128
0.8462	Intermediate Similarity	NPC469644
0.8462	Intermediate Similarity	NPC184302
0.8455	Intermediate Similarity	NPC118286
0.8455	Intermediate Similarity	NPC470700
0.8455	Intermediate Similarity	NPC302681
0.8455	Intermediate Similarity	NPC248904
0.8455	Intermediate Similarity	NPC39097
0.8455	Intermediate Similarity	NPC39664
0.8455	Intermediate Similarity	NPC109691
0.8455	Intermediate Similarity	NPC472797
0.8448	Intermediate Similarity	NPC172219
0.8448	Intermediate Similarity	NPC470760
0.8448	Intermediate Similarity	NPC304510
0.8448	Intermediate Similarity	NPC477136
0.8443	Intermediate Similarity	NPC257947
0.843	Intermediate Similarity	NPC476254
0.843	Intermediate Similarity	NPC131397
0.8426	Intermediate Similarity	NPC100340
0.8426	Intermediate Similarity	NPC143659
0.8417	Intermediate Similarity	NPC96940
0.8396	Intermediate Similarity	NPC312132
0.8396	Intermediate Similarity	NPC259512
0.839	Intermediate Similarity	NPC282255
0.839	Intermediate Similarity	NPC3239
0.839	Intermediate Similarity	NPC69006
0.8378	Intermediate Similarity	NPC54844
0.8376	Intermediate Similarity	NPC144343
0.8364	Intermediate Similarity	NPC474839
0.8364	Intermediate Similarity	NPC117115
0.8362	Intermediate Similarity	NPC38893
0.8362	Intermediate Similarity	NPC477137
0.8362	Intermediate Similarity	NPC308311
0.8333	Intermediate Similarity	NPC122175
0.8333	Intermediate Similarity	NPC120638
0.8333	Intermediate Similarity	NPC294741
0.8318	Intermediate Similarity	NPC474073
0.8305	Intermediate Similarity	NPC151197
0.8305	Intermediate Similarity	NPC191866
0.8304	Intermediate Similarity	NPC61885
0.8304	Intermediate Similarity	NPC63698
0.8291	Intermediate Similarity	NPC33270
0.8291	Intermediate Similarity	NPC69261
0.8288	Intermediate Similarity	NPC21594
0.8286	Intermediate Similarity	NPC295295
0.8279	Intermediate Similarity	NPC293801
0.8276	Intermediate Similarity	NPC192948
0.8276	Intermediate Similarity	NPC232165
0.8276	Intermediate Similarity	NPC35797
0.8276	Intermediate Similarity	NPC808
0.8273	Intermediate Similarity	NPC119860
0.8273	Intermediate Similarity	NPC30506
0.8273	Intermediate Similarity	NPC323810
0.8257	Intermediate Similarity	NPC252105
0.8257	Intermediate Similarity	NPC477685
0.825	Intermediate Similarity	NPC39029
0.825	Intermediate Similarity	NPC212965
0.8246	Intermediate Similarity	NPC469912
0.8246	Intermediate Similarity	NPC151537
0.8241	Intermediate Similarity	NPC299762
0.8241	Intermediate Similarity	NPC33675
0.8241	Intermediate Similarity	NPC80027
0.823	Intermediate Similarity	NPC202647
0.823	Intermediate Similarity	NPC473524
0.822	Intermediate Similarity	NPC469609
0.8214	Intermediate Similarity	NPC151477
0.8214	Intermediate Similarity	NPC474352
0.8205	Intermediate Similarity	NPC150624
0.8205	Intermediate Similarity	NPC469663
0.8205	Intermediate Similarity	NPC123559
0.8205	Intermediate Similarity	NPC92
0.8205	Intermediate Similarity	NPC219112
0.8198	Intermediate Similarity	NPC47284
0.8198	Intermediate Similarity	NPC292452
0.819	Intermediate Similarity	NPC249270
0.8182	Intermediate Similarity	NPC71094
0.8174	Intermediate Similarity	NPC228425
0.8167	Intermediate Similarity	NPC218753
0.8167	Intermediate Similarity	NPC24125
0.8165	Intermediate Similarity	NPC130103
0.8158	Intermediate Similarity	NPC168657
0.8151	Intermediate Similarity	NPC121866
0.8148	Intermediate Similarity	NPC291789
0.8142	Intermediate Similarity	NPC306295
0.8136	Intermediate Similarity	NPC221549
0.8136	Intermediate Similarity	NPC50521
0.8136	Intermediate Similarity	NPC244816
0.8136	Intermediate Similarity	NPC277588
0.813	Intermediate Similarity	NPC33654
0.813	Intermediate Similarity	NPC105031
0.8125	Intermediate Similarity	NPC53740
0.8125	Intermediate Similarity	NPC469913
0.812	Intermediate Similarity	NPC147179
0.812	Intermediate Similarity	NPC53906
0.812	Intermediate Similarity	NPC474486
0.811	Intermediate Similarity	NPC472798
0.8087	Intermediate Similarity	NPC470770
0.8087	Intermediate Similarity	NPC266937
0.8083	Intermediate Similarity	NPC472071
0.8065	Intermediate Similarity	NPC82299
0.8053	Intermediate Similarity	NPC320439
0.8051	Intermediate Similarity	NPC114064
0.8051	Intermediate Similarity	NPC308828

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 NPC319803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	872
0.2-0.3	1709
0.3-0.4	2961
0.4-0.5	1735
0.5-0.6	1150
0.6-0.7	390
0.7-0.8	47
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9619	High Similarity	NPD4750	Phase 3
0.8512	High Similarity	NPD6917	Clinical (unspecified phase)
0.8426	Intermediate Similarity	NPD846	Approved
0.8426	Intermediate Similarity	NPD940	Approved
0.8417	Intermediate Similarity	NPD4749	Approved
0.8396	Intermediate Similarity	NPD288	Approved
0.8387	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD844	Approved
0.8	Intermediate Similarity	NPD1242	Phase 1
0.7909	Intermediate Similarity	NPD3020	Approved
0.7863	Intermediate Similarity	NPD7635	Approved
0.7838	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD845	Approved
0.7769	Intermediate Similarity	NPD3091	Approved
0.7734	Intermediate Similarity	NPD4625	Phase 3
0.7661	Intermediate Similarity	NPD3092	Approved
0.7661	Intermediate Similarity	NPD1610	Phase 2
0.7656	Intermediate Similarity	NPD4908	Phase 1
0.7636	Intermediate Similarity	NPD2860	Approved
0.7636	Intermediate Similarity	NPD2859	Approved
0.7607	Intermediate Similarity	NPD3021	Approved
0.7607	Intermediate Similarity	NPD3022	Approved
0.7597	Intermediate Similarity	NPD3027	Phase 3
0.7586	Intermediate Similarity	NPD2342	Discontinued
0.7559	Intermediate Similarity	NPD3094	Phase 2
0.7545	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2934	Approved
0.7545	Intermediate Similarity	NPD2933	Approved
0.7538	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1809	Phase 2
0.7407	Intermediate Similarity	NPD6099	Approved
0.7407	Intermediate Similarity	NPD6100	Approved
0.7381	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD602	Approved
0.7364	Intermediate Similarity	NPD858	Approved
0.7364	Intermediate Similarity	NPD859	Approved
0.7364	Intermediate Similarity	NPD599	Approved
0.736	Intermediate Similarity	NPD3095	Discontinued
0.735	Intermediate Similarity	NPD1444	Approved
0.735	Intermediate Similarity	NPD1445	Approved
0.7339	Intermediate Similarity	NPD1548	Phase 1
0.7319	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1792	Phase 2
0.7308	Intermediate Similarity	NPD2861	Phase 2
0.7293	Intermediate Similarity	NPD1613	Approved
0.7293	Intermediate Similarity	NPD2238	Phase 2
0.7293	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6671	Approved
0.7222	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2932	Approved
0.7213	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2568	Approved
0.7143	Intermediate Similarity	NPD9093	Approved
0.7132	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3019	Approved
0.7087	Intermediate Similarity	NPD4059	Approved
0.7087	Intermediate Similarity	NPD4626	Approved
0.708	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6696	Suspended
0.7075	Intermediate Similarity	NPD9089	Approved
0.7073	Intermediate Similarity	NPD2229	Approved
0.7073	Intermediate Similarity	NPD2228	Approved
0.7073	Intermediate Similarity	NPD2234	Approved
0.7045	Intermediate Similarity	NPD5736	Approved
0.7045	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD111	Approved
0.7025	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1133	Approved
0.7023	Intermediate Similarity	NPD1131	Approved
0.7023	Intermediate Similarity	NPD1129	Approved
0.7023	Intermediate Similarity	NPD1135	Approved
0.7023	Intermediate Similarity	NPD1134	Approved
0.7016	Intermediate Similarity	NPD9614	Approved
0.7016	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD9618	Approved
0.7	Intermediate Similarity	NPD4659	Approved
0.7	Intermediate Similarity	NPD290	Approved
0.6992	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1201	Approved
0.6977	Remote Similarity	NPD422	Phase 1
0.6963	Remote Similarity	NPD6405	Approved
0.6963	Remote Similarity	NPD6407	Approved
0.695	Remote Similarity	NPD3892	Phase 2
0.6935	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4097	Suspended
0.6929	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2233	Approved
0.6923	Remote Similarity	NPD7390	Discontinued
0.6923	Remote Similarity	NPD2232	Approved
0.6923	Remote Similarity	NPD2230	Approved
0.6912	Remote Similarity	NPD3620	Phase 2
0.6912	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7340	Approved
0.6897	Remote Similarity	NPD9273	Approved
0.6894	Remote Similarity	NPD4103	Phase 2
0.6894	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.688	Remote Similarity	NPD497	Approved
0.6879	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4093	Discontinued
0.6875	Remote Similarity	NPD5691	Approved
0.6861	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5124	Phase 1
0.6857	Remote Similarity	NPD5762	Approved
0.6857	Remote Similarity	NPD5763	Approved
0.685	Remote Similarity	NPD856	Approved
0.685	Remote Similarity	NPD9615	Approved
0.685	Remote Similarity	NPD9613	Approved
0.685	Remote Similarity	NPD9616	Approved
0.685	Remote Similarity	NPD16	Approved
0.6846	Remote Similarity	NPD1091	Approved
0.6838	Remote Similarity	NPD6663	Approved
0.6822	Remote Similarity	NPD9381	Approved
0.6822	Remote Similarity	NPD9384	Approved
0.6822	Remote Similarity	NPD1778	Approved
0.6822	Remote Similarity	NPD1751	Approved
0.6822	Remote Similarity	NPD2286	Discontinued
0.6812	Remote Similarity	NPD1607	Approved
0.6809	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD9500	Approved
0.6803	Remote Similarity	NPD2684	Approved
0.68	Remote Similarity	NPD498	Approved
0.68	Remote Similarity	NPD5283	Phase 1
0.68	Remote Similarity	NPD1398	Phase 1
0.68	Remote Similarity	NPD495	Approved
0.68	Remote Similarity	NPD496	Approved
0.6797	Remote Similarity	NPD7741	Discontinued
0.6797	Remote Similarity	NPD316	Approved
0.6797	Remote Similarity	NPD5304	Approved
0.6797	Remote Similarity	NPD5303	Approved
0.6794	Remote Similarity	NPD2235	Phase 2
0.6794	Remote Similarity	NPD2561	Approved
0.6794	Remote Similarity	NPD2231	Phase 2
0.6794	Remote Similarity	NPD2562	Approved
0.6791	Remote Similarity	NPD3018	Phase 2
0.6788	Remote Similarity	NPD943	Approved
0.6788	Remote Similarity	NPD4060	Phase 1
0.6779	Remote Similarity	NPD37	Approved
0.6774	Remote Similarity	NPD228	Approved
0.6772	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1470	Approved
0.6767	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3553	Approved
0.6763	Remote Similarity	NPD3555	Approved
0.6763	Remote Similarity	NPD3552	Approved
0.6763	Remote Similarity	NPD3554	Approved
0.6746	Remote Similarity	NPD1791	Approved
0.6746	Remote Similarity	NPD1793	Approved
0.6742	Remote Similarity	NPD9622	Approved
0.6741	Remote Similarity	NPD600	Approved
0.6741	Remote Similarity	NPD596	Approved
0.6739	Remote Similarity	NPD5735	Approved
0.6719	Remote Similarity	NPD317	Approved
0.6719	Remote Similarity	NPD318	Approved
0.6714	Remote Similarity	NPD7743	Approved
0.6714	Remote Similarity	NPD7742	Approved
0.6714	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD9094	Approved
0.6693	Remote Similarity	NPD7157	Approved
0.6692	Remote Similarity	NPD8651	Approved
0.6692	Remote Similarity	NPD4589	Approved
0.6667	Remote Similarity	NPD5408	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD5404	Approved
0.6667	Remote Similarity	NPD7330	Discontinued
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD5405	Approved
0.6667	Remote Similarity	NPD5406	Approved
0.6645	Remote Similarity	NPD4965	Approved
0.6645	Remote Similarity	NPD4966	Approved
0.6645	Remote Similarity	NPD4967	Phase 2
0.6644	Remote Similarity	NPD2534	Approved
0.6644	Remote Similarity	NPD2532	Approved
0.6644	Remote Similarity	NPD2533	Approved
0.6643	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5177	Phase 3
0.6642	Remote Similarity	NPD2797	Approved
0.6641	Remote Similarity	NPD1981	Approved
0.6641	Remote Similarity	NPD7636	Approved
0.6641	Remote Similarity	NPD1980	Approved
0.6641	Remote Similarity	NPD1983	Approved
0.6641	Remote Similarity	NPD3496	Discontinued
0.6639	Remote Similarity	NPD3028	Approved
0.6639	Remote Similarity	NPD968	Approved
0.662	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5327	Phase 3
0.6617	Remote Similarity	NPD2983	Phase 2
0.6617	Remote Similarity	NPD2982	Phase 2
0.6604	Remote Similarity	NPD9294	Approved
0.6597	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1510	Phase 2
0.6594	Remote Similarity	NPD839	Approved
0.6594	Remote Similarity	NPD840	Approved
0.6593	Remote Similarity	NPD9620	Approved
0.6593	Remote Similarity	NPD2195	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