NPASS Compound

Structure

NPC145238 OpenBabel07101719252D 40 43 0 0 1 0 0 0 0 0999 V2000 -0.1346 8.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2521 -1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9033 2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 -0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 -1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1197 7.9991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7537 7.5121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7687 6.5122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6421 6.0252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6571 5.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 4.5384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5454 3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4921 -0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 -2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 -3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0938 -4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3011 -1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4452 -3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 -1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7019 2.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 -0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9921 -2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 -2.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7468 -0.9740 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 0.1073 -4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5753 1.5387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5799 -3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 -2.9158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3265 -1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 17 30 1 0 0 0 0 18 22 1 0 0 0 0 18 33 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 20 31 1 1 0 0 0 21 34 2 0 0 0 0 21 40 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 1 0 0 0 24 30 1 6 0 0 0 24 31 1 0 0 0 0 25 35 2 0 0 0 0 25 39 1 0 0 0 0 26 29 1 0 0 0 0 26 32 1 1 0 0 0 27 30 1 0 0 0 0 27 36 2 0 0 0 0 28 32 1 6 0 0 0 28 39 1 0 0 0 0 29 32 1 0 0 0 0 30 37 1 6 0 0 0 31 38 1 1 0 0 0 32 40 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.29
Volume:	577.032
LogP:	3.326
LogD:	2.354
LogS:	-4.3
# Rotatable Bonds:	10
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.18
Synthetic Accessibility Score:	5.367
Fsp3:	0.594
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.722
MDCK Permeability:	1.0038039363280404e-05
Pgp-inhibitor:	0.872
Pgp-substrate:	0.487
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.105

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.525
Plasma Protein Binding (PPB):	69.51663970947266%
Volume Distribution (VD):	1.114
Pgp-substrate:	14.245743751525879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.122
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.662
CYP2C19-substrate:	0.538
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.837
CYP2D6-substrate:	0.663
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	1.344
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.841
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.337
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.872
Carcinogencity:	0.156
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC145238

Natural Product ID:	NPC145238
*Common Name:**	UUDRJPRIBMGADE-YNOQIDMFSA-N
IUPAC Name:	n.a.
Synonyms:	NSC-336793
Standard InCHIKey:	UUDRJPRIBMGADE-YNOQIDMFSA-N
Standard InCHI:	InChI=1S/C32H42O8/c1-7-8-9-10-11-12-13-14-25(35)39-28-20(3)31(38)23(26-29(5,6)32(26,28)40-21(4)34)16-22(18-33)17-30(37)24(31)15-19(2)27(30)36/h9-16,20,23-24,26,28,33,37-38H,7-8,17-18H2,1-6H3/b10-9+,12-11+,14-13+/t20-,23+,24-,26-,28-,30-,31-,32-/m1/s1
SMILES:	CCC/C=C/C=C/C=C/C(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@H]3[C@]1(OC(=O)C)C3(C)C)C=C(C[C@]1([C@H]2C=C(C1=O)C)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446957
PubChem CID:	6450291
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

*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
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.0022	ug ml-1	PMID[479879]

☑ 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 NPC145238 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	248
0.1-0.2	1337
0.2-0.3	3996
0.3-0.4	6481
0.4-0.5	13614
0.5-0.6	9784
0.6-0.7	5800
0.7-0.8	1248
0.8-0.85	69
0.85-0.9	28
0.9-0.95	56
0.95-1	36

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC52839
0.9652	High Similarity	NPC257017
0.9652	High Similarity	NPC162009
0.9649	High Similarity	NPC329080
0.9649	High Similarity	NPC471128
0.9649	High Similarity	NPC471126
0.9649	High Similarity	NPC185876
0.9649	High Similarity	NPC145182
0.9649	High Similarity	NPC157252
0.9649	High Similarity	NPC472759
0.9649	High Similarity	NPC19336
0.9561	High Similarity	NPC156745
0.9561	High Similarity	NPC236918
0.9561	High Similarity	NPC180640
0.9561	High Similarity	NPC5991
0.9561	High Similarity	NPC255081
0.9561	High Similarity	NPC5989
0.9561	High Similarity	NPC471108
0.9561	High Similarity	NPC275696
0.9561	High Similarity	NPC22628
0.9478	High Similarity	NPC475885
0.9474	High Similarity	NPC472760
0.9474	High Similarity	NPC472758
0.9474	High Similarity	NPC171905
0.9474	High Similarity	NPC471125
0.9474	High Similarity	NPC472397
0.9402	High Similarity	NPC472399
0.9386	High Similarity	NPC153651
0.9386	High Similarity	NPC10721
0.9316	High Similarity	NPC19464
0.9304	High Similarity	NPC146280
0.9304	High Similarity	NPC124676
0.9298	High Similarity	NPC234858
0.9298	High Similarity	NPC471127
0.9298	High Similarity	NPC154363
0.9231	High Similarity	NPC472401
0.9217	High Similarity	NPC156252
0.9211	High Similarity	NPC474872
0.9167	High Similarity	NPC471940
0.9123	High Similarity	NPC474937
0.9123	High Similarity	NPC472757
0.9123	High Similarity	NPC71889
0.9091	High Similarity	NPC236999
0.9083	High Similarity	NPC471939
0.9043	High Similarity	NPC472400
0.9035	High Similarity	NPC170212
0.9035	High Similarity	NPC151216
0.9035	High Similarity	NPC221511
0.9035	High Similarity	NPC17138
0.9035	High Similarity	NPC265499
0.9035	High Similarity	NPC475391
0.9035	High Similarity	NPC215643
0.9035	High Similarity	NPC89227
0.9035	High Similarity	NPC101825
0.9	High Similarity	NPC473919
0.9	High Similarity	NPC473709
0.8947	High Similarity	NPC260786
0.8947	High Similarity	NPC96739
0.8947	High Similarity	NPC474871
0.8947	High Similarity	NPC174471
0.8947	High Similarity	NPC158523
0.8947	High Similarity	NPC475937
0.8934	High Similarity	NPC270109
0.8917	High Similarity	NPC473802
0.886	High Similarity	NPC153036
0.877	High Similarity	NPC222307
0.8632	High Similarity	NPC477091
0.8609	High Similarity	NPC163004
0.8583	High Similarity	NPC471136
0.8583	High Similarity	NPC475500
0.8583	High Similarity	NPC472667
0.8583	High Similarity	NPC475154
0.8583	High Similarity	NPC100017
0.8583	High Similarity	NPC223356
0.8583	High Similarity	NPC182266
0.8583	High Similarity	NPC471137
0.8583	High Similarity	NPC473548
0.845	Intermediate Similarity	NPC68282
0.8425	Intermediate Similarity	NPC180902
0.8425	Intermediate Similarity	NPC475139
0.8425	Intermediate Similarity	NPC473485
0.8425	Intermediate Similarity	NPC474508
0.8361	Intermediate Similarity	NPC143755
0.8346	Intermediate Similarity	NPC477189
0.8346	Intermediate Similarity	NPC251564
0.8346	Intermediate Similarity	NPC475606
0.8346	Intermediate Similarity	NPC475314
0.8319	Intermediate Similarity	NPC469454
0.8319	Intermediate Similarity	NPC469496
0.8319	Intermediate Similarity	NPC469463
0.8308	Intermediate Similarity	NPC243902
0.8293	Intermediate Similarity	NPC310511
0.8291	Intermediate Similarity	NPC273433
0.8279	Intermediate Similarity	NPC470186
0.8268	Intermediate Similarity	NPC162495
0.825	Intermediate Similarity	NPC138303
0.825	Intermediate Similarity	NPC133677
0.825	Intermediate Similarity	NPC67290
0.8217	Intermediate Similarity	NPC476111
0.8189	Intermediate Similarity	NPC470850
0.8182	Intermediate Similarity	NPC470793
0.8182	Intermediate Similarity	NPC179626
0.8167	Intermediate Similarity	NPC106395
0.8167	Intermediate Similarity	NPC46269
0.8154	Intermediate Similarity	NPC476823
0.8151	Intermediate Similarity	NPC304180
0.8151	Intermediate Similarity	NPC179798
0.8125	Intermediate Similarity	NPC104382
0.8125	Intermediate Similarity	NPC470851
0.811	Intermediate Similarity	NPC475273
0.811	Intermediate Similarity	NPC168849
0.8099	Intermediate Similarity	NPC73314
0.8085	Intermediate Similarity	NPC472398
0.8083	Intermediate Similarity	NPC138757
0.8083	Intermediate Similarity	NPC123855
0.8083	Intermediate Similarity	NPC76550
0.808	Intermediate Similarity	NPC222688
0.8077	Intermediate Similarity	NPC469674
0.8077	Intermediate Similarity	NPC469673
0.8067	Intermediate Similarity	NPC5103
0.8065	Intermediate Similarity	NPC4548
0.8065	Intermediate Similarity	NPC475003
0.8062	Intermediate Similarity	NPC196921
0.8062	Intermediate Similarity	NPC220757
0.8062	Intermediate Similarity	NPC471170
0.8049	Intermediate Similarity	NPC257457
0.8049	Intermediate Similarity	NPC311554
0.8033	Intermediate Similarity	NPC477509
0.8033	Intermediate Similarity	NPC148458
0.8031	Intermediate Similarity	NPC15095
0.8031	Intermediate Similarity	NPC293112
0.8031	Intermediate Similarity	NPC473635
0.8031	Intermediate Similarity	NPC217901
0.8029	Intermediate Similarity	NPC140021
0.8028	Intermediate Similarity	NPC138641
0.8028	Intermediate Similarity	NPC469648
0.8028	Intermediate Similarity	NPC469647
0.8028	Intermediate Similarity	NPC22571
0.8028	Intermediate Similarity	NPC283875
0.8017	Intermediate Similarity	NPC477126
0.8017	Intermediate Similarity	NPC474271
0.8017	Intermediate Similarity	NPC56448
0.8017	Intermediate Similarity	NPC471204
0.8	Intermediate Similarity	NPC471855
0.8	Intermediate Similarity	NPC475668
0.8	Intermediate Similarity	NPC473921
0.8	Intermediate Similarity	NPC34963
0.8	Intermediate Similarity	NPC475480
0.8	Intermediate Similarity	NPC189393
0.8	Intermediate Similarity	NPC90814
0.8	Intermediate Similarity	NPC470185
0.7984	Intermediate Similarity	NPC221414
0.7984	Intermediate Similarity	NPC35109
0.7984	Intermediate Similarity	NPC231529
0.7984	Intermediate Similarity	NPC471407
0.7984	Intermediate Similarity	NPC469380
0.7984	Intermediate Similarity	NPC175186
0.7967	Intermediate Similarity	NPC471854
0.7967	Intermediate Similarity	NPC469684
0.7967	Intermediate Similarity	NPC23046
0.7966	Intermediate Similarity	NPC143609
0.7966	Intermediate Similarity	NPC67321
0.7966	Intermediate Similarity	NPC187435
0.7953	Intermediate Similarity	NPC172154
0.7953	Intermediate Similarity	NPC81736
0.7949	Intermediate Similarity	NPC118911
0.7939	Intermediate Similarity	NPC58029
0.7937	Intermediate Similarity	NPC23786
0.7937	Intermediate Similarity	NPC470265
0.7934	Intermediate Similarity	NPC317687
0.7923	Intermediate Similarity	NPC279478
0.7923	Intermediate Similarity	NPC473838
0.7923	Intermediate Similarity	NPC475389
0.7923	Intermediate Similarity	NPC241935
0.792	Intermediate Similarity	NPC472004
0.792	Intermediate Similarity	NPC41123
0.792	Intermediate Similarity	NPC114939
0.792	Intermediate Similarity	NPC145074
0.792	Intermediate Similarity	NPC48692
0.7917	Intermediate Similarity	NPC475134
0.7917	Intermediate Similarity	NPC257240
0.7917	Intermediate Similarity	NPC477103
0.7917	Intermediate Similarity	NPC475563
0.7903	Intermediate Similarity	NPC251310
0.7903	Intermediate Similarity	NPC284707
0.7902	Intermediate Similarity	NPC233581
0.7902	Intermediate Similarity	NPC145649
0.7899	Intermediate Similarity	NPC102843
0.7899	Intermediate Similarity	NPC476479
0.7886	Intermediate Similarity	NPC270478
0.7886	Intermediate Similarity	NPC176840
0.7886	Intermediate Similarity	NPC270958
0.7881	Intermediate Similarity	NPC111952
0.7881	Intermediate Similarity	NPC477125
0.7874	Intermediate Similarity	NPC11895
0.7874	Intermediate Similarity	NPC67251
0.7874	Intermediate Similarity	NPC473979
0.7874	Intermediate Similarity	NPC469789
0.7869	Intermediate Similarity	NPC25909
0.7862	Intermediate Similarity	NPC11410

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 NPC145238 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	1619
0.2-0.3	3505
0.3-0.4	2405
0.4-0.5	909
0.5-0.6	334
0.6-0.7	147
0.7-0.8	11
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
0.7917	Intermediate Similarity	NPD6371	Approved
0.7642	Intermediate Similarity	NPD8297	Approved
0.7607	Intermediate Similarity	NPD6648	Approved
0.7542	Intermediate Similarity	NPD5344	Discontinued
0.754	Intermediate Similarity	NPD7115	Discovery
0.748	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6650	Approved
0.7419	Intermediate Similarity	NPD6649	Approved
0.7398	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6319	Approved
0.7328	Intermediate Similarity	NPD7604	Phase 2
0.7317	Intermediate Similarity	NPD6899	Approved
0.7317	Intermediate Similarity	NPD6881	Approved
0.7302	Intermediate Similarity	NPD4632	Approved
0.728	Intermediate Similarity	NPD8130	Phase 1
0.7258	Intermediate Similarity	NPD6372	Approved
0.7258	Intermediate Similarity	NPD6373	Approved
0.7236	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5697	Approved
0.7222	Intermediate Similarity	NPD6882	Approved
0.72	Intermediate Similarity	NPD7290	Approved
0.72	Intermediate Similarity	NPD6883	Approved
0.72	Intermediate Similarity	NPD7102	Approved
0.7167	Intermediate Similarity	NPD7640	Approved
0.7167	Intermediate Similarity	NPD7639	Approved
0.7154	Intermediate Similarity	NPD7128	Approved
0.7154	Intermediate Similarity	NPD5739	Approved
0.7154	Intermediate Similarity	NPD6675	Approved
0.7154	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD6869	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6847	Approved
0.7132	Intermediate Similarity	NPD6009	Approved
0.712	Intermediate Similarity	NPD6013	Approved
0.712	Intermediate Similarity	NPD6014	Approved
0.712	Intermediate Similarity	NPD6012	Approved
0.7111	Intermediate Similarity	NPD7736	Approved
0.7099	Intermediate Similarity	NPD6054	Approved
0.709	Intermediate Similarity	NPD7507	Approved
0.709	Intermediate Similarity	NPD6616	Approved
0.7083	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD7638	Approved
0.7069	Intermediate Similarity	NPD7838	Discovery
0.7059	Intermediate Similarity	NPD7319	Approved
0.7049	Intermediate Similarity	NPD5211	Phase 2
0.7045	Intermediate Similarity	NPD5983	Phase 2
0.704	Intermediate Similarity	NPD6686	Approved
0.704	Intermediate Similarity	NPD6011	Approved
0.704	Intermediate Similarity	NPD7320	Approved
0.7037	Intermediate Similarity	NPD7078	Approved
0.7023	Intermediate Similarity	NPD7516	Approved
0.6992	Remote Similarity	NPD6370	Approved
0.6963	Remote Similarity	NPD6336	Discontinued
0.696	Remote Similarity	NPD5701	Approved
0.6957	Remote Similarity	NPD7260	Phase 2
0.6947	Remote Similarity	NPD7328	Approved
0.6947	Remote Similarity	NPD7327	Approved
0.6942	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD46	Approved
0.6917	Remote Similarity	NPD8515	Approved
0.6917	Remote Similarity	NPD8517	Approved
0.6917	Remote Similarity	NPD7503	Approved
0.6917	Remote Similarity	NPD8516	Approved
0.6917	Remote Similarity	NPD6016	Approved
0.6917	Remote Similarity	NPD8513	Phase 3
0.6917	Remote Similarity	NPD6015	Approved
0.6917	Remote Similarity	NPD6921	Approved
0.6912	Remote Similarity	NPD8293	Discontinued
0.6885	Remote Similarity	NPD4696	Approved
0.6885	Remote Similarity	NPD5286	Approved
0.6885	Remote Similarity	NPD5285	Approved
0.688	Remote Similarity	NPD6008	Approved
0.6866	Remote Similarity	NPD5988	Approved
0.6864	Remote Similarity	NPD7983	Approved
0.6842	Remote Similarity	NPD6059	Approved
0.6833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6053	Discontinued
0.6815	Remote Similarity	NPD8328	Phase 3
0.6797	Remote Similarity	NPD4634	Approved
0.6791	Remote Similarity	NPD8379	Approved
0.6791	Remote Similarity	NPD8033	Approved
0.6791	Remote Similarity	NPD8335	Approved
0.6791	Remote Similarity	NPD8380	Approved
0.6791	Remote Similarity	NPD8296	Approved
0.6791	Remote Similarity	NPD8378	Approved
0.6783	Remote Similarity	NPD1696	Phase 3
0.6774	Remote Similarity	NPD4633	Approved
0.6774	Remote Similarity	NPD5224	Approved
0.6774	Remote Similarity	NPD5226	Approved
0.6774	Remote Similarity	NPD5225	Approved
0.6767	Remote Similarity	NPD7100	Approved
0.6767	Remote Similarity	NPD7101	Approved
0.6744	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6084	Phase 2
0.6721	Remote Similarity	NPD6083	Phase 2
0.6721	Remote Similarity	NPD4755	Approved
0.672	Remote Similarity	NPD5174	Approved
0.672	Remote Similarity	NPD5175	Approved
0.6716	Remote Similarity	NPD8377	Approved
0.6716	Remote Similarity	NPD8294	Approved
0.6694	Remote Similarity	NPD5223	Approved
0.6692	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6641	Remote Similarity	NPD8133	Approved
0.6641	Remote Similarity	NPD4730	Approved
0.6641	Remote Similarity	NPD4729	Approved
0.664	Remote Similarity	NPD7632	Discontinued
0.6639	Remote Similarity	NPD5785	Approved
0.6617	Remote Similarity	NPD6317	Approved
0.6613	Remote Similarity	NPD4700	Approved
0.6612	Remote Similarity	NPD5282	Discontinued
0.6589	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7902	Approved
0.6583	Remote Similarity	NPD7637	Suspended
0.6567	Remote Similarity	NPD6313	Approved
0.6567	Remote Similarity	NPD6314	Approved
0.6557	Remote Similarity	NPD5695	Phase 3
0.6555	Remote Similarity	NPD1695	Approved
0.6549	Remote Similarity	NPD6845	Suspended
0.6544	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5248	Approved
0.6538	Remote Similarity	NPD5251	Approved
0.6538	Remote Similarity	NPD5247	Approved
0.6538	Remote Similarity	NPD5249	Phase 3
0.6538	Remote Similarity	NPD5250	Approved
0.6532	Remote Similarity	NPD5696	Approved
0.6529	Remote Similarity	NPD6399	Phase 3
0.6504	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5221	Approved
0.6504	Remote Similarity	NPD5222	Approved
0.6496	Remote Similarity	NPD1694	Approved
0.6493	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4768	Approved
0.6484	Remote Similarity	NPD4767	Approved
0.6475	Remote Similarity	NPD7748	Approved
0.6452	Remote Similarity	NPD5173	Approved
0.6446	Remote Similarity	NPD6079	Approved
0.6446	Remote Similarity	NPD5284	Approved
0.6446	Remote Similarity	NPD5281	Approved
0.6434	Remote Similarity	NPD6412	Phase 2
0.6423	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6908	Approved
0.6423	Remote Similarity	NPD5210	Approved
0.6423	Remote Similarity	NPD6909	Approved
0.6423	Remote Similarity	NPD4629	Approved
0.6418	Remote Similarity	NPD6868	Approved
0.6412	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7524	Approved
0.6385	Remote Similarity	NPD5128	Approved
0.6383	Remote Similarity	NPD6033	Approved
0.6371	Remote Similarity	NPD4697	Phase 3
0.637	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5216	Approved
0.6364	Remote Similarity	NPD5217	Approved
0.6364	Remote Similarity	NPD5215	Approved
0.6341	Remote Similarity	NPD7900	Approved
0.6341	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7236	Approved
0.6328	Remote Similarity	NPD4754	Approved
0.6311	Remote Similarity	NPD7515	Phase 2
0.6311	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD5693	Phase 1
0.6311	Remote Similarity	NPD5694	Approved
0.6311	Remote Similarity	NPD6050	Approved
0.6299	Remote Similarity	NPD1700	Approved
0.6288	Remote Similarity	NPD5169	Approved
0.6288	Remote Similarity	NPD5135	Approved
0.6288	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5328	Approved
0.6281	Remote Similarity	NPD4753	Phase 2
0.6271	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.626	Remote Similarity	NPD4202	Approved
0.6242	Remote Similarity	NPD7239	Suspended
0.6241	Remote Similarity	NPD5127	Approved
0.624	Remote Similarity	NPD7839	Suspended
0.6239	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5209	Approved
0.623	Remote Similarity	NPD5692	Phase 3
0.6228	Remote Similarity	NPD7799	Discontinued
0.6218	Remote Similarity	NPD5363	Approved
0.6218	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6672	Approved
0.6198	Remote Similarity	NPD5737	Approved
0.6186	Remote Similarity	NPD7154	Phase 3
0.6186	Remote Similarity	NPD6695	Phase 3
0.6186	Remote Similarity	NPD5362	Discontinued
0.6185	Remote Similarity	NPD8434	Phase 2
0.6179	Remote Similarity	NPD8034	Phase 2
0.6179	Remote Similarity	NPD8035	Phase 2
0.6176	Remote Similarity	NPD8368	Discontinued
0.6167	Remote Similarity	NPD5279	Phase 3

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