NPASS Compound

Structure

NPC19464 OpenBabel07101718282D 43 46 0 0 1 0 0 0 0 0999 V2000 -4.3970 -4.4347 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 -3.5385 -4.9476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6651 -4.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8067 -4.9735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9332 -4.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0748 -4.9994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7986 -4.5125 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 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 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 0.8884 1.4869 0.0000 C 0 0 1 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 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 2 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 -0.1969 2.7868 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 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 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 25 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 23 2 0 0 0 0 18 32 1 0 0 0 0 19 23 1 0 0 0 0 19 35 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 21 33 1 6 0 0 0 22 36 2 0 0 0 0 22 43 1 0 0 0 0 23 27 1 0 0 0 0 24 32 1 1 0 0 0 24 33 1 0 0 0 0 25 37 2 0 0 0 0 25 42 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 26 33 1 6 0 0 0 27 38 2 0 0 0 0 28 31 1 0 0 0 0 28 34 1 6 0 0 0 29 32 1 0 0 0 0 29 39 2 0 0 0 0 30 34 1 1 0 0 0 30 42 1 0 0 0 0 31 34 1 0 0 0 0 32 40 1 1 0 0 0 33 41 1 6 0 0 0 34 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.35
Volume:	625.687
LogP:	5.146
LogD:	3.451
LogS:	-4.479
# Rotatable Bonds:	15
TPSA:	147.43
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	5.195
Fsp3:	0.765
Lipinski Rule-of-5:	Rejected
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:	-4.987
MDCK Permeability:	2.118974043696653e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.714
Plasma Protein Binding (PPB):	89.70488739013672%
Volume Distribution (VD):	1.152
Pgp-substrate:	7.238478183746338%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.576
CYP2C19-substrate:	0.363
CYP2C9-inhibitor:	0.796
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	2.772
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.731
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.41
AMES Toxicity:	0.207
Rat Oral Acute Toxicity:	0.402
Maximum Recommended Daily Dose:	0.697
Skin Sensitization:	0.717
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC19464

Natural Product ID:	NPC19464
*Common Name:**	Trigowiin A
IUPAC Name:	n.a.
Synonyms:	Trigowiin A
Standard InCHIKey:	KWBZHXARNUSVGU-SNDKCSAGSA-N
Standard InCHI:	InChI=1S/C34H50O9/c1-7-8-9-10-11-12-13-14-15-16-25(37)42-30-21(3)33(41)24-17-20(2)29(39)32(24,40)18-23(19-35)27(38)26(33)28-31(5,6)34(28,30)43-22(4)36/h17-18,21,24,26,28,30,35,40-41H,7-16,19H2,1-6H3/t21-,24-,26+,28-,30-,32-,33+,34-/m1/s1
SMILES:	CCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2([C@@H]3C=C(C)C(=O)[C@]3(C=C(CO)C(=O)[C@H]2[C@@H]2C(C)(C)[C@]12OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208234
PubChem CID:	71456088
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
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[21520897]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23148674]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23215460]
NPO19424	Trigonostemon howii	Species	Euphorbiaceae	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	100000.0	nM	PMID[475424]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	2.3	n.a.	PMID[475424]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	43500.0	nM	PMID[475424]

☑ 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 NPC19464 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	263
0.1-0.2	1566
0.2-0.3	4591
0.3-0.4	7499
0.4-0.5	13107
0.5-0.6	8674
0.6-0.7	5428
0.7-0.8	1359
0.8-0.85	91
0.85-0.9	44
0.9-0.95	55
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9911	High Similarity	NPC472401
0.9737	High Similarity	NPC472399
0.9732	High Similarity	NPC5991
0.9732	High Similarity	NPC275696
0.9732	High Similarity	NPC5989
0.9732	High Similarity	NPC471108
0.9732	High Similarity	NPC22628
0.9732	High Similarity	NPC255081
0.9643	High Similarity	NPC472758
0.9643	High Similarity	NPC471125
0.9643	High Similarity	NPC171905
0.9643	High Similarity	NPC472397
0.9561	High Similarity	NPC52839
0.9474	High Similarity	NPC157252
0.9474	High Similarity	NPC471128
0.9474	High Similarity	NPC145182
0.9474	High Similarity	NPC471126
0.9381	High Similarity	NPC156252
0.9316	High Similarity	NPC145238
0.931	High Similarity	NPC257017
0.931	High Similarity	NPC162009
0.9286	High Similarity	NPC472757
0.9211	High Similarity	NPC10721
0.9204	High Similarity	NPC472400
0.9153	High Similarity	NPC473919
0.9153	High Similarity	NPC473709
0.9123	High Similarity	NPC154363
0.9123	High Similarity	NPC234858
0.9123	High Similarity	NPC471127
0.9107	High Similarity	NPC475937
0.9107	High Similarity	NPC158523
0.9068	High Similarity	NPC473802
0.9043	High Similarity	NPC153651
0.9035	High Similarity	NPC474872
0.9018	High Similarity	NPC153036
0.9	High Similarity	NPC471940
0.8974	High Similarity	NPC185876
0.8974	High Similarity	NPC19336
0.8974	High Similarity	NPC472759
0.8974	High Similarity	NPC329080
0.8966	High Similarity	NPC146280
0.8966	High Similarity	NPC124676
0.8947	High Similarity	NPC71889
0.8947	High Similarity	NPC474937
0.8926	High Similarity	NPC236999
0.8917	High Similarity	NPC471939
0.8889	High Similarity	NPC156745
0.8889	High Similarity	NPC236918
0.8889	High Similarity	NPC180640
0.886	High Similarity	NPC221511
0.886	High Similarity	NPC215643
0.886	High Similarity	NPC89227
0.886	High Similarity	NPC151216
0.886	High Similarity	NPC17138
0.886	High Similarity	NPC101825
0.886	High Similarity	NPC475391
0.886	High Similarity	NPC265499
0.886	High Similarity	NPC170212
0.8814	High Similarity	NPC475885
0.8803	High Similarity	NPC472760
0.8783	High Similarity	NPC477091
0.8772	High Similarity	NPC474871
0.8772	High Similarity	NPC174471
0.8772	High Similarity	NPC96739
0.8772	High Similarity	NPC260786
0.877	High Similarity	NPC270109
0.8761	High Similarity	NPC163004
0.8607	High Similarity	NPC222307
0.856	High Similarity	NPC475139
0.856	High Similarity	NPC180902
0.8487	Intermediate Similarity	NPC251310
0.8438	Intermediate Similarity	NPC243902
0.8425	Intermediate Similarity	NPC475500
0.8425	Intermediate Similarity	NPC475154
0.8425	Intermediate Similarity	NPC100017
0.8425	Intermediate Similarity	NPC471136
0.8425	Intermediate Similarity	NPC473548
0.8425	Intermediate Similarity	NPC182266
0.8425	Intermediate Similarity	NPC471137
0.8425	Intermediate Similarity	NPC223356
0.8417	Intermediate Similarity	NPC472667
0.84	Intermediate Similarity	NPC162495
0.8387	Intermediate Similarity	NPC168849
0.8387	Intermediate Similarity	NPC475273
0.8361	Intermediate Similarity	NPC222688
0.8319	Intermediate Similarity	NPC179626
0.8306	Intermediate Similarity	NPC217901
0.8295	Intermediate Similarity	NPC68282
0.8281	Intermediate Similarity	NPC476823
0.8276	Intermediate Similarity	NPC273433
0.8268	Intermediate Similarity	NPC473485
0.8268	Intermediate Similarity	NPC474508
0.8264	Intermediate Similarity	NPC472933
0.825	Intermediate Similarity	NPC474654
0.825	Intermediate Similarity	NPC176513
0.825	Intermediate Similarity	NPC470854
0.825	Intermediate Similarity	NPC287343
0.825	Intermediate Similarity	NPC470775
0.825	Intermediate Similarity	NPC97908
0.825	Intermediate Similarity	NPC122033
0.824	Intermediate Similarity	NPC470882
0.8203	Intermediate Similarity	NPC469673
0.8197	Intermediate Similarity	NPC112038
0.8197	Intermediate Similarity	NPC143755
0.8197	Intermediate Similarity	NPC472004
0.819	Intermediate Similarity	NPC29827
0.8189	Intermediate Similarity	NPC475606
0.8189	Intermediate Similarity	NPC251564
0.8189	Intermediate Similarity	NPC475314
0.8189	Intermediate Similarity	NPC196921
0.8189	Intermediate Similarity	NPC477189
0.8189	Intermediate Similarity	NPC220757
0.816	Intermediate Similarity	NPC293112
0.816	Intermediate Similarity	NPC225049
0.816	Intermediate Similarity	NPC473635
0.8151	Intermediate Similarity	NPC472926
0.8151	Intermediate Similarity	NPC477126
0.8151	Intermediate Similarity	NPC7921
0.8151	Intermediate Similarity	NPC208998
0.8145	Intermediate Similarity	NPC67251
0.8136	Intermediate Similarity	NPC287311
0.813	Intermediate Similarity	NPC477046
0.813	Intermediate Similarity	NPC102822
0.813	Intermediate Similarity	NPC310511
0.8125	Intermediate Similarity	NPC189393
0.8125	Intermediate Similarity	NPC34963
0.8125	Intermediate Similarity	NPC90814
0.8115	Intermediate Similarity	NPC470186
0.811	Intermediate Similarity	NPC35109
0.811	Intermediate Similarity	NPC470880
0.811	Intermediate Similarity	NPC231529
0.8103	Intermediate Similarity	NPC474716
0.8099	Intermediate Similarity	NPC472927
0.8099	Intermediate Similarity	NPC472934
0.8099	Intermediate Similarity	NPC471854
0.8099	Intermediate Similarity	NPC469684
0.8095	Intermediate Similarity	NPC473265
0.8095	Intermediate Similarity	NPC473253
0.8083	Intermediate Similarity	NPC473798
0.808	Intermediate Similarity	NPC81736
0.808	Intermediate Similarity	NPC470922
0.808	Intermediate Similarity	NPC172154
0.808	Intermediate Similarity	NPC476729
0.808	Intermediate Similarity	NPC24651
0.8067	Intermediate Similarity	NPC317687
0.8067	Intermediate Similarity	NPC474516
0.8067	Intermediate Similarity	NPC472002
0.8067	Intermediate Similarity	NPC471933
0.8065	Intermediate Similarity	NPC269642
0.8062	Intermediate Similarity	NPC469674
0.8062	Intermediate Similarity	NPC58029
0.8062	Intermediate Similarity	NPC476111
0.8051	Intermediate Similarity	NPC257240
0.8051	Intermediate Similarity	NPC477103
0.8047	Intermediate Similarity	NPC476855
0.8047	Intermediate Similarity	NPC473838
0.8047	Intermediate Similarity	NPC475389
0.8047	Intermediate Similarity	NPC241935
0.8047	Intermediate Similarity	NPC279478
0.8033	Intermediate Similarity	NPC188667
0.8033	Intermediate Similarity	NPC17772
0.8033	Intermediate Similarity	NPC470776
0.8033	Intermediate Similarity	NPC204552
0.8031	Intermediate Similarity	NPC476859
0.8017	Intermediate Similarity	NPC328374
0.8017	Intermediate Similarity	NPC270958
0.8017	Intermediate Similarity	NPC207217
0.8017	Intermediate Similarity	NPC476710
0.8017	Intermediate Similarity	NPC251236
0.8017	Intermediate Similarity	NPC474734
0.8017	Intermediate Similarity	NPC476711
0.8017	Intermediate Similarity	NPC40632
0.8017	Intermediate Similarity	NPC96312
0.8	Intermediate Similarity	NPC105926
0.8	Intermediate Similarity	NPC11895
0.8	Intermediate Similarity	NPC202889
0.8	Intermediate Similarity	NPC73300
0.8	Intermediate Similarity	NPC49451
0.8	Intermediate Similarity	NPC18945
0.8	Intermediate Similarity	NPC962
0.8	Intermediate Similarity	NPC108721
0.8	Intermediate Similarity	NPC91693
0.8	Intermediate Similarity	NPC250109
0.8	Intermediate Similarity	NPC469789
0.8	Intermediate Similarity	NPC265557
0.7984	Intermediate Similarity	NPC159456
0.7984	Intermediate Similarity	NPC472769
0.7984	Intermediate Similarity	NPC4021
0.7984	Intermediate Similarity	NPC470779
0.7983	Intermediate Similarity	NPC317107
0.7983	Intermediate Similarity	NPC146945
0.7983	Intermediate Similarity	NPC171888
0.7983	Intermediate Similarity	NPC157476
0.7969	Intermediate Similarity	NPC476854
0.7969	Intermediate Similarity	NPC470851
0.7967	Intermediate Similarity	NPC77689
0.7967	Intermediate Similarity	NPC473636
0.7967	Intermediate Similarity	NPC470777
0.7967	Intermediate Similarity	NPC211093
0.7967	Intermediate Similarity	NPC477092

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 NPC19464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	2024
0.2-0.3	3642
0.3-0.4	2073
0.4-0.5	755
0.5-0.6	267
0.6-0.7	146
0.7-0.8	14
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
0.8051	Intermediate Similarity	NPD6371	Approved
0.7769	Intermediate Similarity	NPD8297	Approved
0.776	Intermediate Similarity	NPD6319	Approved
0.7583	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6649	Approved
0.7541	Intermediate Similarity	NPD6650	Approved
0.7521	Intermediate Similarity	NPD6372	Approved
0.7521	Intermediate Similarity	NPD6373	Approved
0.752	Intermediate Similarity	NPD7115	Discovery
0.7519	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD7736	Approved
0.748	Intermediate Similarity	NPD6054	Approved
0.7462	Intermediate Similarity	NPD6616	Approved
0.7442	Intermediate Similarity	NPD7604	Phase 2
0.7438	Intermediate Similarity	NPD6881	Approved
0.7438	Intermediate Similarity	NPD6899	Approved
0.7419	Intermediate Similarity	NPD4632	Approved
0.7417	Intermediate Similarity	NPD7128	Approved
0.7417	Intermediate Similarity	NPD6675	Approved
0.7417	Intermediate Similarity	NPD5739	Approved
0.7417	Intermediate Similarity	NPD6402	Approved
0.7405	Intermediate Similarity	NPD8293	Discontinued
0.7405	Intermediate Similarity	NPD7078	Approved
0.7398	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6370	Approved
0.7355	Intermediate Similarity	NPD5697	Approved
0.7344	Intermediate Similarity	NPD6059	Approved
0.7339	Intermediate Similarity	NPD6882	Approved
0.7317	Intermediate Similarity	NPD6883	Approved
0.7317	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7102	Approved
0.7317	Intermediate Similarity	NPD7290	Approved
0.7308	Intermediate Similarity	NPD8328	Phase 3
0.7295	Intermediate Similarity	NPD7320	Approved
0.7293	Intermediate Similarity	NPD7319	Approved
0.7287	Intermediate Similarity	NPD6015	Approved
0.7287	Intermediate Similarity	NPD6016	Approved
0.7258	Intermediate Similarity	NPD6617	Approved
0.7258	Intermediate Similarity	NPD6869	Approved
0.7258	Intermediate Similarity	NPD6847	Approved
0.7244	Intermediate Similarity	NPD6009	Approved
0.7236	Intermediate Similarity	NPD6014	Approved
0.7236	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6013	Approved
0.7236	Intermediate Similarity	NPD6012	Approved
0.7231	Intermediate Similarity	NPD5988	Approved
0.7227	Intermediate Similarity	NPD5344	Discontinued
0.7213	Intermediate Similarity	NPD5701	Approved
0.7203	Intermediate Similarity	NPD4225	Approved
0.7177	Intermediate Similarity	NPD4634	Approved
0.7167	Intermediate Similarity	NPD5211	Phase 2
0.7154	Intermediate Similarity	NPD5983	Phase 2
0.7154	Intermediate Similarity	NPD6011	Approved
0.7131	Intermediate Similarity	NPD6008	Approved
0.7073	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7507	Approved
0.7068	Intermediate Similarity	NPD6336	Discontinued
0.7049	Intermediate Similarity	NPD5141	Approved
0.7023	Intermediate Similarity	NPD6921	Approved
0.7	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD6648	Approved
0.7	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD5286	Approved
0.7	Intermediate Similarity	NPD7639	Approved
0.7	Intermediate Similarity	NPD5285	Approved
0.6984	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7983	Approved
0.6977	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4755	Approved
0.6949	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7638	Approved
0.6899	Remote Similarity	NPD6274	Approved
0.6885	Remote Similarity	NPD5226	Approved
0.6885	Remote Similarity	NPD5224	Approved
0.6885	Remote Similarity	NPD5225	Approved
0.6885	Remote Similarity	NPD4633	Approved
0.688	Remote Similarity	NPD6686	Approved
0.687	Remote Similarity	NPD7101	Approved
0.687	Remote Similarity	NPD7516	Approved
0.687	Remote Similarity	NPD7100	Approved
0.6864	Remote Similarity	NPD5282	Discontinued
0.686	Remote Similarity	NPD4700	Approved
0.6838	Remote Similarity	NPD6033	Approved
0.6833	Remote Similarity	NPD6084	Phase 2
0.6833	Remote Similarity	NPD6083	Phase 2
0.6829	Remote Similarity	NPD5174	Approved
0.6829	Remote Similarity	NPD5175	Approved
0.6803	Remote Similarity	NPD1700	Approved
0.6803	Remote Similarity	NPD5223	Approved
0.6797	Remote Similarity	NPD6053	Discontinued
0.6794	Remote Similarity	NPD7328	Approved
0.6794	Remote Similarity	NPD7327	Approved
0.6794	Remote Similarity	NPD6335	Approved
0.678	Remote Similarity	NPD5779	Approved
0.678	Remote Similarity	NPD5778	Approved
0.6767	Remote Similarity	NPD8515	Approved
0.6767	Remote Similarity	NPD8513	Phase 3
0.6767	Remote Similarity	NPD8516	Approved
0.6767	Remote Similarity	NPD8517	Approved
0.6752	Remote Similarity	NPD46	Approved
0.6752	Remote Similarity	NPD6698	Approved
0.6746	Remote Similarity	NPD4730	Approved
0.6746	Remote Similarity	NPD4729	Approved
0.672	Remote Similarity	NPD4767	Approved
0.672	Remote Similarity	NPD4768	Approved
0.6718	Remote Similarity	NPD6317	Approved
0.6694	Remote Similarity	NPD7902	Approved
0.6693	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6642	Remote Similarity	NPD8379	Approved
0.6642	Remote Similarity	NPD8296	Approved
0.6642	Remote Similarity	NPD8335	Approved
0.6642	Remote Similarity	NPD6908	Approved
0.6642	Remote Similarity	NPD8033	Approved
0.6642	Remote Similarity	NPD6909	Approved
0.6642	Remote Similarity	NPD8378	Approved
0.6642	Remote Similarity	NPD8380	Approved
0.6642	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5250	Approved
0.6641	Remote Similarity	NPD5248	Approved
0.6641	Remote Similarity	NPD5247	Approved
0.6641	Remote Similarity	NPD5249	Phase 3
0.6641	Remote Similarity	NPD5251	Approved
0.6639	Remote Similarity	NPD5696	Approved
0.6639	Remote Similarity	NPD6399	Phase 3
0.6614	Remote Similarity	NPD5128	Approved
0.6612	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5222	Approved
0.6612	Remote Similarity	NPD4697	Phase 3
0.6612	Remote Similarity	NPD5221	Approved
0.661	Remote Similarity	NPD5785	Approved
0.6609	Remote Similarity	NPD1696	Phase 3
0.6583	Remote Similarity	NPD7748	Approved
0.6571	Remote Similarity	NPD7260	Phase 2
0.6567	Remote Similarity	NPD8377	Approved
0.6567	Remote Similarity	NPD8294	Approved
0.656	Remote Similarity	NPD4754	Approved
0.6557	Remote Similarity	NPD5173	Approved
0.6555	Remote Similarity	NPD7637	Suspended
0.6555	Remote Similarity	NPD6079	Approved
0.6535	Remote Similarity	NPD6412	Phase 2
0.6529	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5328	Approved
0.6522	Remote Similarity	NPD8074	Phase 3
0.6515	Remote Similarity	NPD6868	Approved
0.6489	Remote Similarity	NPD8133	Approved
0.648	Remote Similarity	NPD7632	Discontinued
0.6471	Remote Similarity	NPD7838	Discovery
0.6466	Remote Similarity	NPD5363	Approved
0.6462	Remote Similarity	NPD5217	Approved
0.6462	Remote Similarity	NPD5215	Approved
0.6462	Remote Similarity	NPD5216	Approved
0.6462	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7900	Approved
0.6446	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6411	Approved
0.6417	Remote Similarity	NPD7515	Phase 2
0.641	Remote Similarity	NPD5786	Approved
0.6397	Remote Similarity	NPD7503	Approved
0.6393	Remote Similarity	NPD5210	Approved
0.6393	Remote Similarity	NPD4629	Approved
0.6387	Remote Similarity	NPD4753	Phase 2
0.6387	Remote Similarity	NPD1695	Approved
0.6385	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5135	Approved
0.6385	Remote Similarity	NPD5169	Approved
0.6371	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4202	Approved
0.6341	Remote Similarity	NPD7839	Suspended
0.6336	Remote Similarity	NPD5127	Approved
0.6303	Remote Similarity	NPD6672	Approved
0.6303	Remote Similarity	NPD5737	Approved
0.6301	Remote Similarity	NPD6333	Approved
0.6301	Remote Similarity	NPD6334	Approved
0.6294	Remote Similarity	NPD8338	Approved
0.6294	Remote Similarity	NPD6845	Suspended
0.6281	Remote Similarity	NPD8034	Phase 2
0.6281	Remote Similarity	NPD8035	Phase 2
0.6271	Remote Similarity	NPD3618	Phase 1
0.6268	Remote Similarity	NPD5956	Approved
0.625	Remote Similarity	NPD6673	Approved
0.625	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6080	Approved
0.6233	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7524	Approved
0.6218	Remote Similarity	NPD3573	Approved
0.6207	Remote Similarity	NPD4269	Approved
0.6207	Remote Similarity	NPD4270	Approved
0.6194	Remote Similarity	NPD5167	Approved
0.6186	Remote Similarity	NPD1694	Approved
0.6186	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6001	Approved
0.6154	Remote Similarity	NPD6110	Phase 1
0.6154	Remote Similarity	NPD5362	Discontinued
0.6154	Remote Similarity	NPD7154	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