NPASS Compound

Structure

NPC475509 OpenBabel07101719192D 48 52 0 0 1 0 0 0 0 0999 V2000 16.1440 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7450 -2.9120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1288 -3.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0396 0.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5302 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1500 0.4057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.2943 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4447 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5950 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7453 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8956 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0459 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1962 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3465 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4969 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6472 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7975 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9478 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2484 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0589 -0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 -1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6994 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6994 2.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4822 -0.1874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 2.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7854 -2.7080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4822 -1.7749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5491 -1.4717 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6994 0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6994 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.9811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5491 2.4528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2484 2.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5491 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 -0.4906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8497 1.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8497 -0.4906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0981 2.9434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3987 2.9434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 34 2 0 0 0 0 3 34 1 0 0 0 0 4 42 1 0 0 0 0 5 42 1 0 0 0 0 8 45 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 23 41 1 0 0 0 0 24 25 1 0 0 0 0 24 38 1 0 0 0 0 25 39 1 0 0 0 0 26 30 1 0 0 0 0 26 35 1 0 0 0 0 27 32 1 0 0 0 0 27 36 1 0 0 0 0 28 33 1 0 0 0 0 28 37 1 0 0 0 0 29 31 1 0 0 0 0 29 40 1 0 0 0 0 30 43 1 0 0 0 0 31 44 1 0 0 0 0 32 45 1 0 0 0 0 33 46 1 0 0 0 0 35 34 1 1 0 0 0 35 36 1 0 0 0 0 36 43 1 1 0 0 0 37 42 1 0 0 0 0 37 44 1 6 0 0 0 38 43 1 0 0 0 0 38 45 1 0 0 0 0 39 44 1 6 0 0 0 39 46 1 0 0 0 0 40 42 1 0 0 0 0 40 48 1 6 0 0 0 41 47 2 0 0 0 0 41 48 1 0 0 0 0 43 6 1 1 0 0 0 44 7 1 6 0 0 0 45 46 1 6 0 0 0 46 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	664.62
Volume:	773.697
LogP:	12.649
LogD:	7.058
LogS:	-8.308
# Rotatable Bonds:	17
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.093
Synthetic Accessibility Score:	4.801
Fsp3:	0.935
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.07
MDCK Permeability:	6.940070761629613e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	96.29326629638672%
Volume Distribution (VD):	3.131
Pgp-substrate:	1.1941707134246826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.168
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	4.956
Half-life (T1/2):	0.003

ADMET: Toxicity

hERG Blockers:	0.904
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.375
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.561
Skin Sensitization:	0.971
Carcinogencity:	0.008
Eye Corrosion:	0.976
Eye Irritation:	0.657
Respiratory Toxicity:	0.561

Download Data

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

Natural Product: NPC475509

Natural Product ID:	NPC475509
*Common Name:**	Hopenyl Palmitate
IUPAC Name:	[(3S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bS)-5a,5b,8,8,11a,13b-hexamethyl-3-prop-1-en-2-yl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-9-yl] hexadecanoate
Synonyms:	Hopenyl Palmitate
Standard InCHIKey:	HABFHSNAEWDJCC-CBFBYORPSA-N
Standard InCHI:	InChI=1S/C46H80O2/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-41(47)48-40-29-31-44(7)37(42(40,4)5)28-33-46(9)39(44)25-24-38-43(6)30-26-35(34(2)3)36(43)27-32-45(38,46)8/h35-40H,2,10-33H2,1,3-9H3/t35-,36+,37+,38?,39-,40+,43+,44+,45-,46-/m1/s1
SMILES:	CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CCC2[C@@]1(C)CC[C@@H]1[C@]2(C)CC[C@@H]1C(=C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507015
PubChem CID:	44575981
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001823] Hopanoids

*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
NPO12713	Brachylaena ramiflora	Species	Asteraceae	Eukaryota	twigs	Madagascar rainforest	n.a.	PMID[12193040]
NPO12713	Brachylaena ramiflora	Species	Asteraceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	11.6	ug.mL-1	PMID[451248]

☑ 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 NPC475509 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	222
0.1-0.2	1904
0.2-0.3	8120
0.3-0.4	15215
0.4-0.5	5834
0.5-0.6	4882
0.6-0.7	4769
0.7-0.8	1580
0.8-0.85	98
0.85-0.9	50
0.9-0.95	20
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC98270
0.9512	High Similarity	NPC4309
0.9359	High Similarity	NPC305835
0.9268	High Similarity	NPC12774
0.9241	High Similarity	NPC304194
0.9176	High Similarity	NPC160506
0.9176	High Similarity	NPC471901
0.9176	High Similarity	NPC475416
0.9157	High Similarity	NPC33768
0.9146	High Similarity	NPC294438
0.9146	High Similarity	NPC264317
0.907	High Similarity	NPC471902
0.907	High Similarity	NPC473690
0.907	High Similarity	NPC287118
0.9036	High Similarity	NPC2783
0.8987	High Similarity	NPC63020
0.8929	High Similarity	NPC264005
0.8929	High Similarity	NPC269360
0.8902	High Similarity	NPC473742
0.8902	High Similarity	NPC5280
0.8902	High Similarity	NPC471037
0.8875	High Similarity	NPC47808
0.8824	High Similarity	NPC471900
0.8824	High Similarity	NPC16377
0.8824	High Similarity	NPC474719
0.881	High Similarity	NPC329943
0.881	High Similarity	NPC9892
0.881	High Similarity	NPC10005
0.881	High Similarity	NPC91525
0.8795	High Similarity	NPC239362
0.875	High Similarity	NPC303863
0.8721	High Similarity	NPC247312
0.8721	High Similarity	NPC220498
0.8721	High Similarity	NPC57954
0.8721	High Similarity	NPC271974
0.8721	High Similarity	NPC213832
0.8706	High Similarity	NPC46912
0.8706	High Similarity	NPC162107
0.869	High Similarity	NPC474971
0.8675	High Similarity	NPC475726
0.8675	High Similarity	NPC472743
0.8642	High Similarity	NPC471475
0.8636	High Similarity	NPC475061
0.8625	High Similarity	NPC84868
0.8621	High Similarity	NPC471896
0.8621	High Similarity	NPC169933
0.8605	High Similarity	NPC224145
0.859	High Similarity	NPC279241
0.8588	High Similarity	NPC168231
0.8588	High Similarity	NPC471042
0.8588	High Similarity	NPC264127
0.8571	High Similarity	NPC475745
0.8571	High Similarity	NPC264665
0.8571	High Similarity	NPC474482
0.8571	High Similarity	NPC74595
0.8537	High Similarity	NPC261616
0.8537	High Similarity	NPC206735
0.8506	High Similarity	NPC474889
0.8506	High Similarity	NPC475049
0.8506	High Similarity	NPC471043
0.85	High Similarity	NPC92489
0.8471	Intermediate Similarity	NPC292553
0.8452	Intermediate Similarity	NPC139206
0.8452	Intermediate Similarity	NPC170862
0.8444	Intermediate Similarity	NPC279974
0.8427	Intermediate Similarity	NPC291373
0.8427	Intermediate Similarity	NPC244356
0.8427	Intermediate Similarity	NPC224060
0.8415	Intermediate Similarity	NPC192744
0.8409	Intermediate Similarity	NPC113989
0.8409	Intermediate Similarity	NPC175628
0.8409	Intermediate Similarity	NPC111585
0.8409	Intermediate Similarity	NPC120840
0.8409	Intermediate Similarity	NPC148414
0.8395	Intermediate Similarity	NPC68828
0.8391	Intermediate Similarity	NPC474845
0.8391	Intermediate Similarity	NPC472220
0.8391	Intermediate Similarity	NPC97884
0.8391	Intermediate Similarity	NPC146937
0.8372	Intermediate Similarity	NPC98236
0.8372	Intermediate Similarity	NPC472738
0.8372	Intermediate Similarity	NPC269396
0.8353	Intermediate Similarity	NPC474233
0.8352	Intermediate Similarity	NPC327788
0.8333	Intermediate Similarity	NPC277399
0.8315	Intermediate Similarity	NPC60755
0.8315	Intermediate Similarity	NPC285184
0.8315	Intermediate Similarity	NPC77099
0.8315	Intermediate Similarity	NPC470590
0.8315	Intermediate Similarity	NPC470230
0.8315	Intermediate Similarity	NPC26888
0.8313	Intermediate Similarity	NPC170038
0.8295	Intermediate Similarity	NPC11611
0.8295	Intermediate Similarity	NPC30522
0.8276	Intermediate Similarity	NPC4643
0.8276	Intermediate Similarity	NPC474684
0.8276	Intermediate Similarity	NPC57469
0.8276	Intermediate Similarity	NPC142361
0.8261	Intermediate Similarity	NPC469810
0.8256	Intermediate Similarity	NPC201655
0.8242	Intermediate Similarity	NPC205173
0.8242	Intermediate Similarity	NPC84383
0.8235	Intermediate Similarity	NPC245866
0.8222	Intermediate Similarity	NPC470224
0.8222	Intermediate Similarity	NPC294263
0.8222	Intermediate Similarity	NPC474436
0.8222	Intermediate Similarity	NPC49776
0.8222	Intermediate Similarity	NPC475700
0.8222	Intermediate Similarity	NPC86368
0.8222	Intermediate Similarity	NPC63118
0.8214	Intermediate Similarity	NPC195334
0.8214	Intermediate Similarity	NPC290495
0.8202	Intermediate Similarity	NPC474728
0.8193	Intermediate Similarity	NPC201459
0.8193	Intermediate Similarity	NPC118987
0.8182	Intermediate Similarity	NPC40552
0.8182	Intermediate Similarity	NPC472739
0.8182	Intermediate Similarity	NPC246708
0.8172	Intermediate Similarity	NPC119036
0.8172	Intermediate Similarity	NPC472028
0.8171	Intermediate Similarity	NPC143133
0.8171	Intermediate Similarity	NPC298168
0.8171	Intermediate Similarity	NPC66105
0.8161	Intermediate Similarity	NPC472505
0.8161	Intermediate Similarity	NPC325594
0.8161	Intermediate Similarity	NPC28252
0.8161	Intermediate Similarity	NPC187545
0.8161	Intermediate Similarity	NPC55309
0.814	Intermediate Similarity	NPC312660
0.814	Intermediate Similarity	NPC263974
0.8132	Intermediate Similarity	NPC184006
0.8132	Intermediate Similarity	NPC47853
0.8132	Intermediate Similarity	NPC159410
0.8132	Intermediate Similarity	NPC78580
0.8132	Intermediate Similarity	NPC74751
0.8132	Intermediate Similarity	NPC296164
0.8132	Intermediate Similarity	NPC23621
0.8118	Intermediate Similarity	NPC289486
0.8118	Intermediate Similarity	NPC472504
0.8118	Intermediate Similarity	NPC286786
0.8118	Intermediate Similarity	NPC61107
0.8118	Intermediate Similarity	NPC476458
0.8118	Intermediate Similarity	NPC163236
0.8118	Intermediate Similarity	NPC258153
0.809	Intermediate Similarity	NPC470588
0.809	Intermediate Similarity	NPC475921
0.809	Intermediate Similarity	NPC474704
0.8085	Intermediate Similarity	NPC94906
0.8068	Intermediate Similarity	NPC88716
0.8068	Intermediate Similarity	NPC130577
0.8068	Intermediate Similarity	NPC142415
0.8068	Intermediate Similarity	NPC233836
0.8068	Intermediate Similarity	NPC68160
0.8068	Intermediate Similarity	NPC242468
0.8068	Intermediate Similarity	NPC51700
0.8068	Intermediate Similarity	NPC171203
0.8068	Intermediate Similarity	NPC187376
0.8068	Intermediate Similarity	NPC134197
0.8068	Intermediate Similarity	NPC307426
0.8068	Intermediate Similarity	NPC102683
0.8068	Intermediate Similarity	NPC18064
0.8068	Intermediate Similarity	NPC293564
0.8068	Intermediate Similarity	NPC98442
0.8068	Intermediate Similarity	NPC159046
0.8065	Intermediate Similarity	NPC253586
0.8049	Intermediate Similarity	NPC246445
0.8046	Intermediate Similarity	NPC470223
0.8046	Intermediate Similarity	NPC76518
0.8043	Intermediate Similarity	NPC280877
0.8043	Intermediate Similarity	NPC474727
0.8043	Intermediate Similarity	NPC195715
0.8043	Intermediate Similarity	NPC184848
0.8043	Intermediate Similarity	NPC210214
0.8043	Intermediate Similarity	NPC23241
0.8043	Intermediate Similarity	NPC69548
0.8043	Intermediate Similarity	NPC470229
0.8043	Intermediate Similarity	NPC98639
0.8023	Intermediate Similarity	NPC472740
0.8023	Intermediate Similarity	NPC132386
0.8022	Intermediate Similarity	NPC474185
0.8	Intermediate Similarity	NPC328141
0.8	Intermediate Similarity	NPC474484
0.8	Intermediate Similarity	NPC474842
0.8	Intermediate Similarity	NPC103754
0.8	Intermediate Similarity	NPC75941
0.8	Intermediate Similarity	NPC20388
0.8	Intermediate Similarity	NPC108476
0.8	Intermediate Similarity	NPC475951
0.8	Intermediate Similarity	NPC475965
0.7978	Intermediate Similarity	NPC473242
0.7978	Intermediate Similarity	NPC290690
0.7978	Intermediate Similarity	NPC242864
0.7978	Intermediate Similarity	NPC474512
0.7978	Intermediate Similarity	NPC470629
0.7978	Intermediate Similarity	NPC182797
0.7978	Intermediate Similarity	NPC52169
0.7978	Intermediate Similarity	NPC181225
0.7978	Intermediate Similarity	NPC255176
0.7978	Intermediate Similarity	NPC17733
0.7978	Intermediate Similarity	NPC28227

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 NPC475509 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	2285
0.2-0.3	4205
0.3-0.4	1644
0.4-0.5	401
0.5-0.6	172
0.6-0.7	192
0.7-0.8	49
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9176	High Similarity	NPD8035	Phase 2
0.9176	High Similarity	NPD8034	Phase 2
0.9146	High Similarity	NPD7520	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD7748	Approved
0.8132	Intermediate Similarity	NPD7900	Approved
0.7955	Intermediate Similarity	NPD6409	Approved
0.7955	Intermediate Similarity	NPD6684	Approved
0.7955	Intermediate Similarity	NPD5330	Approved
0.7955	Intermediate Similarity	NPD7146	Approved
0.7955	Intermediate Similarity	NPD7521	Approved
0.7955	Intermediate Similarity	NPD7334	Approved
0.7872	Intermediate Similarity	NPD7902	Approved
0.7831	Intermediate Similarity	NPD6117	Approved
0.7826	Intermediate Similarity	NPD6399	Phase 3
0.7805	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5777	Approved
0.7778	Intermediate Similarity	NPD6903	Approved
0.7778	Intermediate Similarity	NPD6672	Approved
0.7778	Intermediate Similarity	NPD5737	Approved
0.7738	Intermediate Similarity	NPD6116	Phase 1
0.7717	Intermediate Similarity	NPD7515	Phase 2
0.7647	Intermediate Similarity	NPD6114	Approved
0.7647	Intermediate Similarity	NPD6697	Approved
0.7647	Intermediate Similarity	NPD6118	Approved
0.7647	Intermediate Similarity	NPD6115	Approved
0.7556	Intermediate Similarity	NPD6098	Approved
0.7528	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7474	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7638	Approved
0.7416	Intermediate Similarity	NPD4788	Approved
0.7363	Intermediate Similarity	NPD3618	Phase 1
0.7349	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7640	Approved
0.7347	Intermediate Similarity	NPD7639	Approved
0.734	Intermediate Similarity	NPD6079	Approved
0.7327	Intermediate Similarity	NPD6402	Approved
0.7327	Intermediate Similarity	NPD7128	Approved
0.7327	Intermediate Similarity	NPD5739	Approved
0.7327	Intermediate Similarity	NPD6675	Approved
0.7312	Intermediate Similarity	NPD6904	Approved
0.7312	Intermediate Similarity	NPD6080	Approved
0.7312	Intermediate Similarity	NPD6673	Approved
0.7303	Intermediate Similarity	NPD3667	Approved
0.7283	Intermediate Similarity	NPD3573	Approved
0.7204	Intermediate Similarity	NPD5208	Approved
0.7188	Intermediate Similarity	NPD6001	Approved
0.7184	Intermediate Similarity	NPD7320	Approved
0.7184	Intermediate Similarity	NPD6881	Approved
0.7184	Intermediate Similarity	NPD6899	Approved
0.7157	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD3668	Phase 3
0.7115	Intermediate Similarity	NPD6373	Approved
0.7115	Intermediate Similarity	NPD6372	Approved
0.7108	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3702	Approved
0.7087	Intermediate Similarity	NPD5697	Approved
0.7087	Intermediate Similarity	NPD5701	Approved
0.7083	Intermediate Similarity	NPD4202	Approved
0.7079	Intermediate Similarity	NPD7525	Registered
0.7075	Intermediate Similarity	NPD8297	Approved
0.7048	Intermediate Similarity	NPD7290	Approved
0.7048	Intermediate Similarity	NPD7102	Approved
0.7048	Intermediate Similarity	NPD6883	Approved
0.7019	Intermediate Similarity	NPD6011	Approved
0.7009	Intermediate Similarity	NPD8133	Approved
0.6988	Remote Similarity	NPD5360	Phase 3
0.6988	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6617	Approved
0.6981	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6869	Approved
0.6981	Remote Similarity	NPD6847	Approved
0.6981	Remote Similarity	NPD6650	Approved
0.6981	Remote Similarity	NPD6649	Approved
0.6979	Remote Similarity	NPD5693	Phase 1
0.6979	Remote Similarity	NPD6050	Approved
0.6966	Remote Similarity	NPD7645	Phase 2
0.6957	Remote Similarity	NPD3665	Phase 1
0.6957	Remote Similarity	NPD3666	Approved
0.6957	Remote Similarity	NPD3133	Approved
0.6952	Remote Similarity	NPD6013	Approved
0.6952	Remote Similarity	NPD6012	Approved
0.6952	Remote Similarity	NPD6014	Approved
0.6951	Remote Similarity	NPD4224	Phase 2
0.6947	Remote Similarity	NPD6051	Approved
0.6941	Remote Similarity	NPD6081	Approved
0.6939	Remote Similarity	NPD5695	Phase 3
0.6923	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6882	Approved
0.69	Remote Similarity	NPD5696	Approved
0.6897	Remote Similarity	NPD3703	Phase 2
0.6875	Remote Similarity	NPD5207	Approved
0.6875	Remote Similarity	NPD5692	Phase 3
0.6869	Remote Similarity	NPD5221	Approved
0.6869	Remote Similarity	NPD4697	Phase 3
0.6869	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5222	Approved
0.6863	Remote Similarity	NPD7632	Discontinued
0.6824	Remote Similarity	NPD4789	Approved
0.6824	Remote Similarity	NPD4245	Approved
0.6824	Remote Similarity	NPD4244	Approved
0.6818	Remote Similarity	NPD7115	Discovery
0.6804	Remote Similarity	NPD5694	Approved
0.68	Remote Similarity	NPD4755	Approved
0.68	Remote Similarity	NPD5173	Approved
0.6739	Remote Similarity	NPD4221	Approved
0.6739	Remote Similarity	NPD4223	Phase 3
0.6727	Remote Similarity	NPD6868	Approved
0.6706	Remote Similarity	NPD3698	Phase 2
0.6705	Remote Similarity	NPD7339	Approved
0.6705	Remote Similarity	NPD6942	Approved
0.6702	Remote Similarity	NPD5329	Approved
0.6702	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6632	Remote Similarity	NPD5279	Phase 3
0.6628	Remote Similarity	NPD4747	Approved
0.6627	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6335	Approved
0.6602	Remote Similarity	NPD5223	Approved
0.6598	Remote Similarity	NPD4753	Phase 2
0.6596	Remote Similarity	NPD4197	Approved
0.6577	Remote Similarity	NPD6274	Approved
0.6552	Remote Similarity	NPD4758	Discontinued
0.6549	Remote Similarity	NPD7100	Approved
0.6549	Remote Similarity	NPD7101	Approved
0.6545	Remote Similarity	NPD6858	Approved
0.6545	Remote Similarity	NPD7094	Approved
0.6545	Remote Similarity	NPD4632	Approved
0.6538	Remote Similarity	NPD5224	Approved
0.6538	Remote Similarity	NPD5211	Phase 2
0.6538	Remote Similarity	NPD5226	Approved
0.6538	Remote Similarity	NPD5225	Approved
0.6538	Remote Similarity	NPD4633	Approved
0.6535	Remote Similarity	NPD7732	Phase 3
0.6525	Remote Similarity	NPD7736	Approved
0.6518	Remote Similarity	NPD6317	Approved
0.6512	Remote Similarity	NPD4137	Phase 3
0.6496	Remote Similarity	NPD7507	Approved
0.6484	Remote Similarity	NPD3671	Phase 1
0.6484	Remote Similarity	NPD3617	Approved
0.6481	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4754	Approved
0.6476	Remote Similarity	NPD6052	Approved
0.6476	Remote Similarity	NPD5174	Approved
0.6476	Remote Similarity	NPD5175	Approved
0.6465	Remote Similarity	NPD5281	Approved
0.6465	Remote Similarity	NPD6411	Approved
0.6465	Remote Similarity	NPD5284	Approved
0.646	Remote Similarity	NPD6314	Approved
0.646	Remote Similarity	NPD6313	Approved
0.6458	Remote Similarity	NPD4688	Approved
0.6458	Remote Similarity	NPD5205	Approved
0.6458	Remote Similarity	NPD4693	Phase 3
0.6458	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4690	Approved
0.6458	Remote Similarity	NPD4138	Approved
0.6458	Remote Similarity	NPD4689	Approved
0.6449	Remote Similarity	NPD6412	Phase 2
0.6444	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4691	Approved
0.6436	Remote Similarity	NPD5654	Approved
0.6435	Remote Similarity	NPD6908	Approved
0.6435	Remote Similarity	NPD6909	Approved
0.6429	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5141	Approved
0.6404	Remote Similarity	NPD5733	Approved
0.6395	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6009	Approved
0.6355	Remote Similarity	NPD4767	Approved
0.6355	Remote Similarity	NPD4768	Approved
0.6348	Remote Similarity	NPD6319	Approved
0.6346	Remote Similarity	NPD8418	Phase 2
0.6333	Remote Similarity	NPD7319	Approved
0.6333	Remote Similarity	NPD8039	Approved
0.6325	Remote Similarity	NPD7604	Phase 2
0.6325	Remote Similarity	NPD8328	Phase 3
0.6322	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5959	Approved
0.6304	Remote Similarity	NPD5364	Discontinued
0.6304	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8293	Discontinued
0.63	Remote Similarity	NPD7637	Suspended
0.6296	Remote Similarity	NPD6614	Approved
0.6296	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5983	Phase 2
0.6293	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5280	Approved
0.6289	Remote Similarity	NPD5690	Phase 2

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