NPASS Compound

Structure

NPC16964 OpenBabel07101718232D 36 37 0 0 1 0 0 0 0 0999 V2000 -5.2602 -1.8683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0138 -3.2662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3740 -0.7455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7049 -0.0023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4538 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4856 1.2435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9079 0.6901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9769 -3.7355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9892 -3.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6062 -2.9584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6309 -2.6455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8772 -1.2476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2848 -1.5555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5188 -0.3140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 -1.3990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6358 -1.2322 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 -7.8268 -0.6444 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 -6.2479 -2.0248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6432 -2.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1481 0.4631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9387 -0.4655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4448 -0.6444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.3959 -0.9534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1358 0.3067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7898 1.3967 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5681 0.3117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6038 -1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1358 0.3067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 21 2 0 0 0 0 12 22 2 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 18 26 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 23 29 1 0 0 0 0 23 31 1 6 0 0 0 24 30 1 0 0 0 0 24 32 1 1 0 0 0 25 27 1 6 0 0 0 25 35 1 0 0 0 0 26 28 1 1 0 0 0 26 36 1 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 29 7 1 1 0 0 0 29 35 1 0 0 0 0 30 8 1 6 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.39
Volume:	557.792
LogP:	4.218
LogD:	3.675
LogS:	-3.94
# Rotatable Bonds:	13
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.197
Synthetic Accessibility Score:	5.11
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.781
MDCK Permeability:	1.6618634617771022e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.478
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	93.98355865478516%
Volume Distribution (VD):	0.97
Pgp-substrate:	4.999962329864502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.595
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.562
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	6.1
Half-life (T1/2):	0.216

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.756
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.716
Skin Sensitization:	0.942
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.052

Download Data

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

Natural Product: NPC16964

Natural Product ID:	NPC16964
*Common Name:**	Ekeberin D4
IUPAC Name:	(1R,4E,8E,12R)-1,12-bis[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,9-dimethyldodeca-4,8-diene-1,12-diol
Synonyms:	Ekeberin D4
Standard InCHIKey:	PIXGUMZAPNRCDR-SFCCXYMXSA-N
Standard InCHI:	InChI=1S/C30H54O6/c1-21(13-15-23(31)29(7)19-17-25(35-29)27(3,4)33)11-9-10-12-22(2)14-16-24(32)30(8)20-18-26(36-30)28(5,6)34/h11-12,23-26,31-34H,9-10,13-20H2,1-8H3/b21-11+,22-12+/t23-,24-,25-,26-,29+,30+/m1/s1
SMILES:	C/C(=CCC/C=C(C)/CC[C@H]([C@]1(C)CC[C@H](C(C)(C)O)O1)O)/CC[C@H]([C@]1(C)CC[C@H](C(C)(C)O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255488
PubChem CID:	24800894
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO9975	Ekebergia capensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220356]
NPO9975	Ekebergia capensis	Species	Meliaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	40000.0	nM	PMID[504807]

☑ 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 NPC16964 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	169
0.1-0.2	1539
0.2-0.3	8189
0.3-0.4	16288
0.4-0.5	8810
0.5-0.6	6428
0.6-0.7	1204
0.7-0.8	60
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9403	High Similarity	NPC306085
0.8889	High Similarity	NPC3852
0.8767	High Similarity	NPC476701
0.8714	High Similarity	NPC476709
0.8551	High Similarity	NPC472947
0.8493	Intermediate Similarity	NPC476703
0.8378	Intermediate Similarity	NPC181838
0.8378	Intermediate Similarity	NPC137345
0.8219	Intermediate Similarity	NPC12696
0.8158	Intermediate Similarity	NPC472948
0.8	Intermediate Similarity	NPC52012
0.7971	Intermediate Similarity	NPC250836
0.7969	Intermediate Similarity	NPC281590
0.7805	Intermediate Similarity	NPC476708
0.7746	Intermediate Similarity	NPC193029
0.7746	Intermediate Similarity	NPC473357
0.7746	Intermediate Similarity	NPC259299
0.7714	Intermediate Similarity	NPC471200
0.7671	Intermediate Similarity	NPC129630
0.7662	Intermediate Similarity	NPC477089
0.7639	Intermediate Similarity	NPC305698
0.7632	Intermediate Similarity	NPC256720
0.7632	Intermediate Similarity	NPC170148
0.7632	Intermediate Similarity	NPC236228
0.7632	Intermediate Similarity	NPC293223
0.76	Intermediate Similarity	NPC471525
0.76	Intermediate Similarity	NPC190859
0.7536	Intermediate Similarity	NPC64971
0.7532	Intermediate Similarity	NPC477427
0.7532	Intermediate Similarity	NPC474826
0.7532	Intermediate Similarity	NPC477426
0.7532	Intermediate Similarity	NPC477425
0.7532	Intermediate Similarity	NPC40049
0.75	Intermediate Similarity	NPC36479
0.75	Intermediate Similarity	NPC82337
0.75	Intermediate Similarity	NPC73603
0.7439	Intermediate Similarity	NPC298595
0.7439	Intermediate Similarity	NPC475206
0.7436	Intermediate Similarity	NPC68119
0.7436	Intermediate Similarity	NPC13823
0.7432	Intermediate Similarity	NPC470041
0.7412	Intermediate Similarity	NPC158388
0.7412	Intermediate Similarity	NPC478004
0.7412	Intermediate Similarity	NPC478003
0.7403	Intermediate Similarity	NPC329626
0.7381	Intermediate Similarity	NPC309656
0.7381	Intermediate Similarity	NPC476706
0.7381	Intermediate Similarity	NPC476707
0.7381	Intermediate Similarity	NPC476704
0.7353	Intermediate Similarity	NPC41180
0.7353	Intermediate Similarity	NPC152438
0.7349	Intermediate Similarity	NPC247826
0.7326	Intermediate Similarity	NPC12172
0.7326	Intermediate Similarity	NPC208886
0.7324	Intermediate Similarity	NPC476702
0.7297	Intermediate Similarity	NPC304690
0.7297	Intermediate Similarity	NPC329989
0.7297	Intermediate Similarity	NPC239373
0.7297	Intermediate Similarity	NPC74722
0.7294	Intermediate Similarity	NPC473564
0.7286	Intermediate Similarity	NPC475251
0.7284	Intermediate Similarity	NPC477385
0.7284	Intermediate Similarity	NPC477390
0.7284	Intermediate Similarity	NPC472465
0.7262	Intermediate Similarity	NPC476948
0.7262	Intermediate Similarity	NPC179659
0.726	Intermediate Similarity	NPC472255
0.726	Intermediate Similarity	NPC472253
0.726	Intermediate Similarity	NPC163290
0.725	Intermediate Similarity	NPC103634
0.725	Intermediate Similarity	NPC100697
0.7246	Intermediate Similarity	NPC278202
0.7246	Intermediate Similarity	NPC122239
0.7241	Intermediate Similarity	NPC98193
0.7241	Intermediate Similarity	NPC81419
0.7241	Intermediate Similarity	NPC179746
0.7229	Intermediate Similarity	NPC290731
0.7209	Intermediate Similarity	NPC476004
0.7209	Intermediate Similarity	NPC474761
0.7209	Intermediate Similarity	NPC472466
0.72	Intermediate Similarity	NPC471781
0.7195	Intermediate Similarity	NPC231601
0.7164	Intermediate Similarity	NPC223604
0.7164	Intermediate Similarity	NPC227135
0.7162	Intermediate Similarity	NPC272961
0.7162	Intermediate Similarity	NPC470040
0.716	Intermediate Similarity	NPC246621
0.716	Intermediate Similarity	NPC5361
0.716	Intermediate Similarity	NPC118116
0.716	Intermediate Similarity	NPC474894
0.7143	Intermediate Similarity	NPC469694
0.7143	Intermediate Similarity	NPC311163
0.7143	Intermediate Similarity	NPC160540
0.7126	Intermediate Similarity	NPC472468
0.7126	Intermediate Similarity	NPC30515
0.7126	Intermediate Similarity	NPC208839
0.7126	Intermediate Similarity	NPC476705
0.7126	Intermediate Similarity	NPC184463
0.7123	Intermediate Similarity	NPC267027
0.7123	Intermediate Similarity	NPC272125
0.7123	Intermediate Similarity	NPC311736
0.7105	Intermediate Similarity	NPC41886
0.7093	Intermediate Similarity	NPC133450
0.7093	Intermediate Similarity	NPC307411
0.7089	Intermediate Similarity	NPC84360
0.7083	Intermediate Similarity	NPC309300
0.7067	Intermediate Similarity	NPC101622
0.7059	Intermediate Similarity	NPC248602
0.7059	Intermediate Similarity	NPC189777
0.7037	Intermediate Similarity	NPC474592
0.7037	Intermediate Similarity	NPC200446
0.7033	Intermediate Similarity	NPC309493
0.7024	Intermediate Similarity	NPC471494
0.7013	Intermediate Similarity	NPC329763
0.7013	Intermediate Similarity	NPC143576
0.7013	Intermediate Similarity	NPC477085
0.7011	Intermediate Similarity	NPC51004
0.7011	Intermediate Similarity	NPC470832
0.7011	Intermediate Similarity	NPC177668
0.7	Intermediate Similarity	NPC218817
0.7	Intermediate Similarity	NPC475931
0.7	Intermediate Similarity	NPC11796
0.6988	Remote Similarity	NPC239308
0.6988	Remote Similarity	NPC11620
0.6988	Remote Similarity	NPC320548
0.6988	Remote Similarity	NPC471340
0.6986	Remote Similarity	NPC238352
0.6986	Remote Similarity	NPC61503
0.6986	Remote Similarity	NPC477009
0.6986	Remote Similarity	NPC308844
0.6986	Remote Similarity	NPC473722
0.6977	Remote Similarity	NPC177629
0.6977	Remote Similarity	NPC202672
0.6977	Remote Similarity	NPC58219
0.6977	Remote Similarity	NPC231784
0.6974	Remote Similarity	NPC4299
0.6966	Remote Similarity	NPC472467
0.6962	Remote Similarity	NPC268111
0.6962	Remote Similarity	NPC315261
0.6962	Remote Similarity	NPC126969
0.6962	Remote Similarity	NPC469880
0.6951	Remote Similarity	NPC77003
0.6944	Remote Similarity	NPC473508
0.6944	Remote Similarity	NPC279200
0.6941	Remote Similarity	NPC477387
0.6941	Remote Similarity	NPC477389
0.6941	Remote Similarity	NPC476217
0.6933	Remote Similarity	NPC273508
0.6933	Remote Similarity	NPC209327
0.6933	Remote Similarity	NPC224532
0.6932	Remote Similarity	NPC210268
0.6914	Remote Similarity	NPC86971
0.6914	Remote Similarity	NPC209995
0.6914	Remote Similarity	NPC233295
0.6905	Remote Similarity	NPC186155
0.6905	Remote Similarity	NPC78673
0.6905	Remote Similarity	NPC3464
0.6905	Remote Similarity	NPC9868
0.6905	Remote Similarity	NPC474780
0.6905	Remote Similarity	NPC151176
0.6905	Remote Similarity	NPC475963
0.6905	Remote Similarity	NPC160517
0.6905	Remote Similarity	NPC319238
0.6897	Remote Similarity	NPC92974
0.6897	Remote Similarity	NPC97103
0.6897	Remote Similarity	NPC477917
0.6897	Remote Similarity	NPC115607
0.6897	Remote Similarity	NPC473058
0.6892	Remote Similarity	NPC137163
0.6889	Remote Similarity	NPC36954
0.6883	Remote Similarity	NPC477087
0.6883	Remote Similarity	NPC477086
0.6875	Remote Similarity	NPC130136
0.6867	Remote Similarity	NPC20072
0.6867	Remote Similarity	NPC329829
0.6867	Remote Similarity	NPC11332
0.6867	Remote Similarity	NPC73310
0.6867	Remote Similarity	NPC180363
0.6867	Remote Similarity	NPC475159
0.6867	Remote Similarity	NPC145914
0.6867	Remote Similarity	NPC131002
0.6867	Remote Similarity	NPC473780
0.6867	Remote Similarity	NPC473529
0.6867	Remote Similarity	NPC65930
0.6867	Remote Similarity	NPC94875
0.6867	Remote Similarity	NPC103171
0.6867	Remote Similarity	NPC473712
0.686	Remote Similarity	NPC474174
0.686	Remote Similarity	NPC251808
0.686	Remote Similarity	NPC186148
0.686	Remote Similarity	NPC477388
0.686	Remote Similarity	NPC477386
0.6857	Remote Similarity	NPC226848
0.6857	Remote Similarity	NPC475830
0.6854	Remote Similarity	NPC476300
0.6854	Remote Similarity	NPC212486
0.6854	Remote Similarity	NPC475912
0.6854	Remote Similarity	NPC61275
0.6849	Remote Similarity	NPC225415
0.6849	Remote Similarity	NPC287744

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 NPC16964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	2298
0.2-0.3	4279
0.3-0.4	1726
0.4-0.5	480
0.5-0.6	183
0.6-0.7	31
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7262	Intermediate Similarity	NPD7524	Approved
0.6988	Remote Similarity	NPD6695	Phase 3
0.6962	Remote Similarity	NPD6933	Approved
0.6905	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6924	Approved
0.6709	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6629	Remote Similarity	NPD7838	Discovery
0.6627	Remote Similarity	NPD6931	Approved
0.6627	Remote Similarity	NPD6930	Phase 2
0.6506	Remote Similarity	NPD6929	Approved
0.6463	Remote Similarity	NPD6932	Approved
0.6444	Remote Similarity	NPD46	Approved
0.6444	Remote Similarity	NPD6698	Approved
0.6438	Remote Similarity	NPD1145	Discontinued
0.6429	Remote Similarity	NPD7525	Registered
0.6374	Remote Similarity	NPD7983	Approved
0.6374	Remote Similarity	NPD7087	Discontinued
0.6351	Remote Similarity	NPD368	Approved
0.631	Remote Similarity	NPD6683	Phase 2
0.6292	Remote Similarity	NPD4251	Approved
0.6292	Remote Similarity	NPD4250	Approved
0.6265	Remote Similarity	NPD5776	Phase 2
0.6265	Remote Similarity	NPD6925	Approved
0.625	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6893	Approved
0.6237	Remote Similarity	NPD5282	Discontinued
0.6235	Remote Similarity	NPD7509	Discontinued
0.6235	Remote Similarity	NPD7332	Phase 2
0.6235	Remote Similarity	NPD7514	Phase 3
0.622	Remote Similarity	NPD7339	Approved
0.622	Remote Similarity	NPD6942	Approved
0.6207	Remote Similarity	NPD7154	Phase 3
0.6207	Remote Similarity	NPD5362	Discontinued
0.6203	Remote Similarity	NPD6922	Approved
0.6203	Remote Similarity	NPD6923	Approved
0.62	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD342	Phase 1
0.619	Remote Similarity	NPD7145	Approved
0.6186	Remote Similarity	NPD5344	Discontinued
0.618	Remote Similarity	NPD4249	Approved
0.6163	Remote Similarity	NPD5369	Approved
0.6163	Remote Similarity	NPD6898	Phase 1
0.6145	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD7144	Approved
0.6125	Remote Similarity	NPD7143	Approved
0.6118	Remote Similarity	NPD7645	Phase 2
0.6104	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD6435	Approved
0.6087	Remote Similarity	NPD3168	Discontinued
0.6049	Remote Similarity	NPD7150	Approved
0.6049	Remote Similarity	NPD7151	Approved
0.6049	Remote Similarity	NPD7152	Approved
0.6047	Remote Similarity	NPD4821	Approved
0.6047	Remote Similarity	NPD4820	Approved
0.6047	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4819	Approved
0.6047	Remote Similarity	NPD4822	Approved
0.6026	Remote Similarity	NPD7331	Phase 2
0.6023	Remote Similarity	NPD5331	Approved
0.6023	Remote Similarity	NPD5332	Approved
0.6023	Remote Similarity	NPD6110	Phase 1
0.6	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4225	Approved
0.5979	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD6902	Approved
0.5977	Remote Similarity	NPD4790	Discontinued
0.5976	Remote Similarity	NPD4732	Discontinued
0.5974	Remote Similarity	NPD3197	Phase 1
0.5962	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5779	Approved
0.5957	Remote Similarity	NPD5778	Approved
0.5934	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.589	Remote Similarity	NPD2267	Suspended
0.5889	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6412	Phase 2
0.5865	Remote Similarity	NPD6371	Approved
0.5862	Remote Similarity	NPD5368	Approved
0.5854	Remote Similarity	NPD4243	Approved
0.5851	Remote Similarity	NPD7637	Suspended
0.5833	Remote Similarity	NPD8264	Approved
0.5825	Remote Similarity	NPD6686	Approved
0.5821	Remote Similarity	NPD4265	Approved
0.5816	Remote Similarity	NPD7638	Approved
0.5814	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD4271	Approved
0.5814	Remote Similarity	NPD4268	Approved
0.5806	Remote Similarity	NPD6101	Approved
0.5806	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6640	Phase 3
0.5778	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD4786	Approved
0.5769	Remote Similarity	NPD371	Approved
0.5758	Remote Similarity	NPD7640	Approved
0.5758	Remote Similarity	NPD6648	Approved
0.5758	Remote Similarity	NPD7639	Approved
0.5733	Remote Similarity	NPD6109	Phase 1
0.573	Remote Similarity	NPD4270	Approved
0.573	Remote Similarity	NPD3667	Approved
0.573	Remote Similarity	NPD4269	Approved
0.5714	Remote Similarity	NPD4785	Approved
0.5714	Remote Similarity	NPD4784	Approved
0.5696	Remote Similarity	NPD7341	Phase 2
0.5684	Remote Similarity	NPD6411	Approved
0.567	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5786	Approved
0.5638	Remote Similarity	NPD1695	Approved
0.5636	Remote Similarity	NPD7327	Approved
0.5636	Remote Similarity	NPD7328	Approved
0.5631	Remote Similarity	NPD5357	Phase 1
0.5625	Remote Similarity	NPD6399	Phase 3
0.5612	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD7839	Suspended
0.5606	Remote Similarity	NPD8957	Approved
0.5604	Remote Similarity	NPD3133	Approved
0.5604	Remote Similarity	NPD3666	Approved
0.5604	Remote Similarity	NPD3665	Phase 1

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