NPASS Compound

Structure

NPC40779 OpenBabel07101719252D 31 32 0 0 1 0 0 0 0 0999 V2000 -10.2438 -3.2876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5309 -2.1286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 1.0828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9418 0.0123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4965 -0.4161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6036 1.4986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9055 -1.8013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8837 -1.5934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9344 2.2418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5817 1.7065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2290 1.1713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8981 0.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2364 -1.0581 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 -10.5528 -2.3365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 2.0339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2509 0.9634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8763 0.6361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5454 -0.1071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.1853 1.5871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2886 0.5621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 21 2 0 0 0 0 11 22 1 0 0 0 0 12 23 2 0 0 0 0 13 25 2 0 0 0 0 14 26 2 0 0 0 0 15 17 1 0 0 0 0 15 22 2 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 24 2 0 0 0 0 20 29 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 29 1 0 0 0 0 27 28 1 0 0 0 0 27 30 1 6 0 0 0 28 5 1 1 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	423.31
Volume:	485.853
LogP:	6.61
LogD:	4.898
LogS:	-3.959
# Rotatable Bonds:	12
TPSA:	56.25
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	3.782
Fsp3:	0.5
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:	-4.795
MDCK Permeability:	2.1113983166287653e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.633
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.81
30% Bioavailability (F30%):	0.16

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.209
Plasma Protein Binding (PPB):	99.01236724853516%
Volume Distribution (VD):	1.768
Pgp-substrate:	1.678772211074829%

ADMET: Metabolism

CYP1A2-inhibitor:	0.753
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.7
CYP2C19-substrate:	0.262
CYP2C9-inhibitor:	0.77
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.916
CYP2D6-substrate:	0.441
CYP3A4-inhibitor:	0.897
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	6.405
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.806
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.958
Carcinogencity:	0.019
Eye Corrosion:	0.004
Eye Irritation:	0.105
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC40779

Natural Product ID:	NPC40779
*Common Name:**	(6S,7R,10E,14E)-16-(1H-Indol-3-Yl)-2,6,10,14-Tetramethylhexadeca-2,10,14-Triene-6,7-Diol
IUPAC Name:	(6S,7R,10E,14E)-16-(1H-indol-3-yl)-2,6,10,14-tetramethylhexadeca-2,10,14-triene-6,7-diol
Synonyms:
Standard InCHIKey:	QSCZFXVTYWFEJV-IQRZJAOQSA-N
Standard InCHI:	InChI=1S/C28H41NO2/c1-21(2)10-9-19-28(5,31)27(30)18-16-23(4)12-8-11-22(3)15-17-24-20-29-26-14-7-6-13-25(24)26/h6-7,10,12-15,20,27,29-31H,8-9,11,16-19H2,1-5H3/b22-15+,23-12+/t27-,28+/m1/s1
SMILES:	CC(=CCC[C@@](C)([C@@H](CC/C(=C/CC/C(=C/Cc1c[nH]c2ccccc12)/C)/C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408945
PubChem CID:	72163131
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
NPO32542	penicillium camemberti oucmdz-1492	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23886345]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	34100.0	nM	PMID[491202]

☑ 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 NPC40779 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	256
0.1-0.2	1873
0.2-0.3	16141
0.3-0.4	16731
0.4-0.5	3536
0.5-0.6	2022
0.6-0.7	1398
0.7-0.8	594
0.8-0.85	89
0.85-0.9	41
0.9-0.95	15
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9477	High Similarity	NPC311276
0.947	High Similarity	NPC469762
0.9404	High Similarity	NPC469785
0.9272	High Similarity	NPC469760
0.9272	High Similarity	NPC73952
0.9272	High Similarity	NPC469786
0.9272	High Similarity	NPC469765
0.9272	High Similarity	NPC469763
0.9272	High Similarity	NPC25008
0.9272	High Similarity	NPC259644
0.9211	High Similarity	NPC80597
0.9211	High Similarity	NPC212376
0.9211	High Similarity	NPC211572
0.9211	High Similarity	NPC75540
0.9211	High Similarity	NPC70922
0.9051	High Similarity	NPC201700
0.9	High Similarity	NPC314372
0.891	High Similarity	NPC230869
0.8889	High Similarity	NPC24678
0.8889	High Similarity	NPC105818
0.8868	High Similarity	NPC160105
0.8867	High Similarity	NPC190296
0.8841	High Similarity	NPC300688
0.8834	High Similarity	NPC151939
0.875	High Similarity	NPC49954
0.875	High Similarity	NPC54988
0.875	High Similarity	NPC474561
0.8742	High Similarity	NPC102423
0.8733	High Similarity	NPC469768
0.8733	High Similarity	NPC469779
0.8733	High Similarity	NPC469767
0.8733	High Similarity	NPC469783
0.8733	High Similarity	NPC469780
0.8733	High Similarity	NPC469761
0.8733	High Similarity	NPC469784
0.8704	High Similarity	NPC470498
0.8679	High Similarity	NPC282231
0.8675	High Similarity	NPC469766
0.865	High Similarity	NPC313791
0.865	High Similarity	NPC314603
0.8627	High Similarity	NPC159856
0.8623	High Similarity	NPC469358
0.8616	High Similarity	NPC279918
0.8591	High Similarity	NPC29886
0.8591	High Similarity	NPC261195
0.858	High Similarity	NPC63751
0.8563	High Similarity	NPC233936
0.8543	High Similarity	NPC73767
0.8533	High Similarity	NPC84911
0.8521	High Similarity	NPC188387
0.8521	High Similarity	NPC163421
0.8516	High Similarity	NPC471957
0.8512	High Similarity	NPC163055
0.8509	High Similarity	NPC194640
0.85	High Similarity	NPC131718
0.8471	Intermediate Similarity	NPC315555
0.8467	Intermediate Similarity	NPC96102
0.8421	Intermediate Similarity	NPC110126
0.8411	Intermediate Similarity	NPC105127
0.8383	Intermediate Similarity	NPC68354
0.8383	Intermediate Similarity	NPC248454
0.8373	Intermediate Similarity	NPC275305
0.8373	Intermediate Similarity	NPC37423
0.8363	Intermediate Similarity	NPC474707
0.8354	Intermediate Similarity	NPC78020
0.8343	Intermediate Similarity	NPC71037
0.8333	Intermediate Similarity	NPC213468
0.8324	Intermediate Similarity	NPC95783
0.8323	Intermediate Similarity	NPC92796
0.8323	Intermediate Similarity	NPC135141
0.8322	Intermediate Similarity	NPC82295
0.8314	Intermediate Similarity	NPC317030
0.8286	Intermediate Similarity	NPC474177
0.8274	Intermediate Similarity	NPC59269
0.8266	Intermediate Similarity	NPC65215
0.8266	Intermediate Similarity	NPC173028
0.8256	Intermediate Similarity	NPC235684
0.8247	Intermediate Similarity	NPC279081
0.8239	Intermediate Similarity	NPC216713
0.8239	Intermediate Similarity	NPC133366
0.8225	Intermediate Similarity	NPC176199
0.8225	Intermediate Similarity	NPC215795
0.8225	Intermediate Similarity	NPC270009
0.8214	Intermediate Similarity	NPC267885
0.8208	Intermediate Similarity	NPC204565
0.8198	Intermediate Similarity	NPC280290
0.8193	Intermediate Similarity	NPC194411
0.8187	Intermediate Similarity	NPC200214
0.8176	Intermediate Similarity	NPC53947
0.8155	Intermediate Similarity	NPC149155
0.8155	Intermediate Similarity	NPC472586
0.8155	Intermediate Similarity	NPC203468
0.8155	Intermediate Similarity	NPC110500
0.815	Intermediate Similarity	NPC94752
0.8137	Intermediate Similarity	NPC470507
0.8129	Intermediate Similarity	NPC230002
0.8118	Intermediate Similarity	NPC126709
0.8118	Intermediate Similarity	NPC55772
0.8118	Intermediate Similarity	NPC248041
0.8101	Intermediate Similarity	NPC288838
0.8095	Intermediate Similarity	NPC34508
0.8092	Intermediate Similarity	NPC62510
0.8086	Intermediate Similarity	NPC285469
0.8079	Intermediate Similarity	NPC267343
0.8066	Intermediate Similarity	NPC475506
0.8066	Intermediate Similarity	NPC300183
0.8059	Intermediate Similarity	NPC111275
0.8057	Intermediate Similarity	NPC213629
0.8047	Intermediate Similarity	NPC329688
0.8047	Intermediate Similarity	NPC189812
0.8043	Intermediate Similarity	NPC46225
0.8035	Intermediate Similarity	NPC228835
0.8025	Intermediate Similarity	NPC471458
0.8022	Intermediate Similarity	NPC155143
0.8022	Intermediate Similarity	NPC476874
0.8012	Intermediate Similarity	NPC283219
0.8012	Intermediate Similarity	NPC472443
0.8011	Intermediate Similarity	NPC154339
0.8011	Intermediate Similarity	NPC470497
0.8	Intermediate Similarity	NPC470499
0.8	Intermediate Similarity	NPC473640
0.8	Intermediate Similarity	NPC127677
0.8	Intermediate Similarity	NPC314957
0.8	Intermediate Similarity	NPC321911
0.8	Intermediate Similarity	NPC37548
0.7989	Intermediate Similarity	NPC314002
0.7987	Intermediate Similarity	NPC143872
0.7978	Intermediate Similarity	NPC98715
0.7977	Intermediate Similarity	NPC472444
0.7977	Intermediate Similarity	NPC48938
0.7964	Intermediate Similarity	NPC49217
0.7956	Intermediate Similarity	NPC100321
0.7953	Intermediate Similarity	NPC145885
0.7953	Intermediate Similarity	NPC14113
0.7953	Intermediate Similarity	NPC84827
0.7952	Intermediate Similarity	NPC469813
0.7952	Intermediate Similarity	NPC476446
0.7952	Intermediate Similarity	NPC78375
0.7943	Intermediate Similarity	NPC171171
0.7937	Intermediate Similarity	NPC179787
0.7937	Intermediate Similarity	NPC469811
0.7937	Intermediate Similarity	NPC201380
0.7933	Intermediate Similarity	NPC195239
0.7933	Intermediate Similarity	NPC157828
0.7931	Intermediate Similarity	NPC204717
0.7927	Intermediate Similarity	NPC129721
0.7927	Intermediate Similarity	NPC286427
0.7923	Intermediate Similarity	NPC193761
0.7917	Intermediate Similarity	NPC317430
0.7917	Intermediate Similarity	NPC154293
0.7907	Intermediate Similarity	NPC11126
0.7904	Intermediate Similarity	NPC470508
0.7901	Intermediate Similarity	NPC470823
0.7892	Intermediate Similarity	NPC16667
0.7889	Intermediate Similarity	NPC251090
0.7889	Intermediate Similarity	NPC11445
0.7886	Intermediate Similarity	NPC15102
0.7882	Intermediate Similarity	NPC97525
0.7882	Intermediate Similarity	NPC472123
0.7879	Intermediate Similarity	NPC56765
0.7879	Intermediate Similarity	NPC41257
0.7879	Intermediate Similarity	NPC318065
0.7879	Intermediate Similarity	NPC206819
0.7875	Intermediate Similarity	NPC63545
0.7874	Intermediate Similarity	NPC139291
0.7874	Intermediate Similarity	NPC220765
0.7874	Intermediate Similarity	NPC472108
0.7862	Intermediate Similarity	NPC242556
0.7861	Intermediate Similarity	NPC198339
0.7853	Intermediate Similarity	NPC141926
0.7853	Intermediate Similarity	NPC325903
0.7853	Intermediate Similarity	NPC321708
0.7849	Intermediate Similarity	NPC225821
0.7849	Intermediate Similarity	NPC323927
0.7845	Intermediate Similarity	NPC229332
0.7831	Intermediate Similarity	NPC151976
0.7831	Intermediate Similarity	NPC473320
0.7829	Intermediate Similarity	NPC165495
0.7829	Intermediate Similarity	NPC165201
0.7821	Intermediate Similarity	NPC150259
0.7821	Intermediate Similarity	NPC99666
0.7818	Intermediate Similarity	NPC216643
0.7816	Intermediate Similarity	NPC192270
0.7807	Intermediate Similarity	NPC258062
0.7805	Intermediate Similarity	NPC34844
0.7805	Intermediate Similarity	NPC207726
0.7805	Intermediate Similarity	NPC38736
0.7798	Intermediate Similarity	NPC42372
0.7797	Intermediate Similarity	NPC17059
0.7797	Intermediate Similarity	NPC119700
0.7797	Intermediate Similarity	NPC46580
0.7791	Intermediate Similarity	NPC470233
0.7778	Intermediate Similarity	NPC22079
0.7778	Intermediate Similarity	NPC307963
0.7778	Intermediate Similarity	NPC187951
0.7771	Intermediate Similarity	NPC19679
0.7771	Intermediate Similarity	NPC472109
0.7771	Intermediate Similarity	NPC472110
0.7771	Intermediate Similarity	NPC67056
0.7766	Intermediate Similarity	NPC223791

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 NPC40779 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	566
0.2-0.3	940
0.3-0.4	1593
0.4-0.5	2822
0.5-0.6	2049
0.6-0.7	821
0.7-0.8	182
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD4184	Clinical (unspecified phase)
0.8543	High Similarity	NPD786	Approved
0.8503	High Similarity	NPD6595	Phase 3
0.8494	Intermediate Similarity	NPD2144	Approved
0.8467	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD4076	Approved
0.8443	Intermediate Similarity	NPD4079	Approved
0.8383	Intermediate Similarity	NPD3505	Approved
0.8383	Intermediate Similarity	NPD3506	Approved
0.8343	Intermediate Similarity	NPD3038	Discontinued
0.8312	Intermediate Similarity	NPD1722	Approved
0.8263	Intermediate Similarity	NPD5065	Approved
0.8228	Intermediate Similarity	NPD3100	Discontinued
0.8214	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD2172	Phase 1
0.8155	Intermediate Similarity	NPD482	Approved
0.8113	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD8431	Approved
0.8081	Intermediate Similarity	NPD2092	Phase 2
0.8081	Intermediate Similarity	NPD2095	Phase 2
0.8081	Intermediate Similarity	NPD2094	Phase 2
0.8063	Intermediate Similarity	NPD4462	Approved
0.8063	Intermediate Similarity	NPD4463	Approved
0.8059	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD2091	Phase 2
0.8035	Intermediate Similarity	NPD2096	Phase 2
0.7989	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD1403	Approved
0.7939	Intermediate Similarity	NPD1404	Approved
0.7917	Intermediate Similarity	NPD4638	Approved
0.7917	Intermediate Similarity	NPD4640	Approved
0.7917	Intermediate Similarity	NPD4639	Approved
0.7882	Intermediate Similarity	NPD750	Phase 2
0.7857	Intermediate Similarity	NPD2642	Approved
0.7857	Intermediate Similarity	NPD2639	Approved
0.7853	Intermediate Similarity	NPD2837	Discontinued
0.7836	Intermediate Similarity	NPD4128	Approved
0.7811	Intermediate Similarity	NPD2641	Approved
0.7811	Intermediate Similarity	NPD2640	Approved
0.7811	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD7957	Phase 1
0.7796	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1038	Approved
0.7747	Intermediate Similarity	NPD7948	Phase 1
0.7746	Intermediate Similarity	NPD4181	Approved
0.7742	Intermediate Similarity	NPD8272	Phase 2
0.7738	Intermediate Similarity	NPD3323	Discontinued
0.773	Intermediate Similarity	NPD8073	Approved
0.7716	Intermediate Similarity	NPD4703	Approved
0.7716	Intermediate Similarity	NPD4702	Approved
0.7713	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5021	Discontinued
0.7701	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4075	Phase 2
0.7688	Intermediate Similarity	NPD8072	Approved
0.7684	Intermediate Similarity	NPD5067	Phase 2
0.7684	Intermediate Similarity	NPD5066	Phase 2
0.768	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1325	Approved
0.7661	Intermediate Similarity	NPD1326	Approved
0.7632	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD2928	Phase 2
0.7625	Intermediate Similarity	NPD1592	Phase 3
0.7598	Intermediate Similarity	NPD3961	Discontinued
0.7598	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD802	Phase 2
0.7566	Intermediate Similarity	NPD1392	Approved
0.7557	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD8122	Approved
0.7543	Intermediate Similarity	NPD8123	Approved
0.7541	Intermediate Similarity	NPD7618	Phase 3
0.7541	Intermediate Similarity	NPD7619	Phase 3
0.7541	Intermediate Similarity	NPD7944	Discontinued
0.7531	Intermediate Similarity	NPD5254	Discontinued
0.7529	Intermediate Similarity	NPD5140	Approved
0.7529	Intermediate Similarity	NPD5138	Approved
0.7528	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3116	Approved
0.7514	Intermediate Similarity	NPD3610	Approved
0.7514	Intermediate Similarity	NPD3609	Approved
0.7514	Intermediate Similarity	NPD3117	Approved
0.7514	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8386	Phase 2
0.75	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1661	Suspended
0.7486	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3654	Approved
0.7474	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD5596	Phase 2
0.7471	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3717	Discontinued
0.7447	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3475	Approved
0.7436	Intermediate Similarity	NPD3476	Approved
0.7425	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7470	Discontinued
0.7394	Intermediate Similarity	NPD4547	Phase 3
0.7386	Intermediate Similarity	NPD2381	Approved
0.7386	Intermediate Similarity	NPD2382	Approved
0.7386	Intermediate Similarity	NPD2380	Approved
0.7382	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD3825	Phase 3
0.7374	Intermediate Similarity	NPD5105	Approved
0.7374	Intermediate Similarity	NPD5106	Approved
0.7371	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6664	Approved
0.7362	Intermediate Similarity	NPD2006	Phase 2
0.736	Intermediate Similarity	NPD5897	Approved
0.736	Intermediate Similarity	NPD5898	Approved
0.736	Intermediate Similarity	NPD5899	Approved
0.736	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD991	Phase 2
0.7355	Intermediate Similarity	NPD2118	Approved
0.7355	Intermediate Similarity	NPD2119	Approved
0.7353	Intermediate Similarity	NPD5255	Approved
0.7349	Intermediate Similarity	NPD2430	Phase 2
0.7348	Intermediate Similarity	NPD6217	Discontinued
0.7348	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5612	Discontinued
0.7344	Intermediate Similarity	NPD2509	Approved
0.7344	Intermediate Similarity	NPD2510	Approved
0.734	Intermediate Similarity	NPD484	Approved
0.7337	Intermediate Similarity	NPD3404	Approved
0.7337	Intermediate Similarity	NPD6026	Approved
0.7337	Intermediate Similarity	NPD2580	Discontinued
0.7333	Intermediate Similarity	NPD4957	Phase 2
0.7329	Intermediate Similarity	NPD2896	Discontinued
0.7326	Intermediate Similarity	NPD8129	Discovery
0.732	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8408	Discontinued
0.7305	Intermediate Similarity	NPD3835	Phase 3
0.7305	Intermediate Similarity	NPD3833	Phase 3
0.7302	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5862	Discovery
0.7296	Intermediate Similarity	NPD3385	Approved
0.7294	Intermediate Similarity	NPD2581	Approved
0.7294	Intermediate Similarity	NPD2582	Approved
0.7292	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5901	Discontinued
0.7277	Intermediate Similarity	NPD5426	Phase 3
0.7273	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8026	Phase 1
0.7267	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD4601	Approved
0.7249	Intermediate Similarity	NPD4600	Approved
0.7243	Intermediate Similarity	NPD4615	Phase 2
0.724	Intermediate Similarity	NPD3003	Approved
0.7229	Intermediate Similarity	NPD1683	Approved
0.7228	Intermediate Similarity	NPD6281	Approved
0.7225	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8322	Phase 2
0.7198	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5555	Phase 1
0.7196	Intermediate Similarity	NPD1768	Approved
0.7194	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD8093	Discontinued
0.7193	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4030	Approved
0.7188	Intermediate Similarity	NPD4028	Approved
0.7188	Intermediate Similarity	NPD4029	Approved
0.7182	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2165	Phase 1
0.716	Intermediate Similarity	NPD1262	Discovery
0.7157	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD8094	Discontinued
0.715	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7558	Phase 2
0.7143	Intermediate Similarity	NPD6178	Phase 3
0.7143	Intermediate Similarity	NPD1248	Discontinued
0.7143	Intermediate Similarity	NPD5611	Phase 2
0.7136	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3113	Approved
0.7135	Intermediate Similarity	NPD3112	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