NPASS Compound

Structure

CID2745 OpenBabel06191715322D 35 38 0 0 1 0 0 0 0 0999 V2000 -9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 6 9 1 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 17 2 0 0 0 0 10 19 1 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 22 2 0 0 0 0 13 17 1 0 0 0 0 13 23 2 0 0 0 0 14 19 1 0 0 0 0 14 25 1 0 0 0 0 15 24 1 0 0 0 0 15 29 1 0 0 0 0 19 26 2 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 24 33 1 1 0 0 0 25 28 1 0 0 0 0 25 29 1 1 0 0 0 26 35 1 0 0 0 0 27 28 1 0 0 0 0 27 34 1 1 0 0 0 29 5 1 1 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	648.39
Volume:	659.866
LogP:	3.919
LogD:	3.669
LogS:	-3.19
# Rotatable Bonds:	5
TPSA:	173.98
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.189
Synthetic Accessibility Score:	5.387
Fsp3:	0.889
Lipinski Rule-of-5:	Rejected
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:	-5.998
MDCK Permeability:	1.3297405530465767e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.844
20% Bioavailability (F20%):	0.395
30% Bioavailability (F30%):	0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	92.35987091064453%
Volume Distribution (VD):	0.406
Pgp-substrate:	4.161101341247559%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.237
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.573
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	0.99
Half-life (T1/2):	0.435

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.245
Skin Sensitization:	0.016
Carcinogencity:	0.034
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC2745

Natural Product ID:	NPC2745
*Common Name:**	Vedelianin
IUPAC Name:	(2S,3R,4aR,9aR)-7-[(E)-2-[3,5-dihydroxy-4-(3-methylbut-2-enyl)phenyl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,3,5-triol
Synonyms:	Vedelianin
Standard InCHIKey:	OYMAGMAEFPAAGU-HKYLTJPLSA-N
Standard InCHI:	InChI=1S/C29H36O6/c1-16(2)6-9-20-21(30)11-18(12-22(20)31)8-7-17-10-19-14-25-28(3,4)27(34)24(33)15-29(25,5)35-26(19)23(32)13-17/h6-8,10-13,24-25,27,30-34H,9,14-15H2,1-5H3/b8-7+/t24-,25-,27-,29-/m1/s1
SMILES:	CC(=CCc1c(cc(/C=C/c2cc3C[C@@H]4C(C)(C)[C@@H]([C@@H](C[C@@]4(C)Oc3c(c2)O)O)O)cc1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL223046
PubChem CID:	643539
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(92)80315-6]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11421757]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15974621]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	Krachong waterfall area, Trang Province, Thailand	2001-APR	PMID[15974621]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[17326683]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17326683]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28972755]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27255	Macaranga alnifolia	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	2
GI50	1
IC50	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	130.0	nM	PMID[540201]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	190.0	nM	PMID[540203]
NPT1535	Cell Line	U-87 MG	Homo sapiens	EC50	=	30.0	nM	PMID[540203]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	80.0	nM	PMID[540202]

☑ 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 NPC2745 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	503
0.1-0.2	1554
0.2-0.3	3735
0.3-0.4	8835
0.4-0.5	9709
0.5-0.6	4148
0.6-0.7	7237
0.7-0.8	5708
0.8-0.85	857
0.85-0.9	355
0.9-0.95	48
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC157783
0.993	High Similarity	NPC158784
0.993	High Similarity	NPC195561
0.9861	High Similarity	NPC302915
0.9793	High Similarity	NPC325860
0.979	High Similarity	NPC212142
0.9517	High Similarity	NPC473876
0.9448	High Similarity	NPC474397
0.9444	High Similarity	NPC90645
0.9444	High Similarity	NPC472457
0.9392	High Similarity	NPC160196
0.9379	High Similarity	NPC233980
0.9375	High Similarity	NPC473845
0.9301	High Similarity	NPC35216
0.9267	High Similarity	NPC188578
0.9267	High Similarity	NPC80918
0.9241	High Similarity	NPC473108
0.9241	High Similarity	NPC50250
0.9236	High Similarity	NPC323126
0.9236	High Similarity	NPC204347
0.9236	High Similarity	NPC59841
0.9236	High Similarity	NPC2613
0.9236	High Similarity	NPC475891
0.9184	High Similarity	NPC16269
0.9184	High Similarity	NPC21776
0.9184	High Similarity	NPC101376
0.9178	High Similarity	NPC469557
0.9167	High Similarity	NPC471389
0.9167	High Similarity	NPC265075
0.9161	High Similarity	NPC70682
0.9161	High Similarity	NPC260741
0.9128	High Similarity	NPC477612
0.9116	High Similarity	NPC260397
0.911	High Similarity	NPC45257
0.911	High Similarity	NPC93323
0.911	High Similarity	NPC469795
0.911	High Similarity	NPC280092
0.911	High Similarity	NPC12641
0.911	High Similarity	NPC63879
0.9097	High Similarity	NPC198038
0.9097	High Similarity	NPC259519
0.906	High Similarity	NPC211561
0.9041	High Similarity	NPC85264
0.9041	High Similarity	NPC102044
0.9041	High Similarity	NPC474104
0.9041	High Similarity	NPC47633
0.9041	High Similarity	NPC477616
0.9034	High Similarity	NPC263261
0.9034	High Similarity	NPC87725
0.9034	High Similarity	NPC178054
0.9028	High Similarity	NPC184613
0.9028	High Similarity	NPC127218
0.9028	High Similarity	NPC245207
0.9028	High Similarity	NPC32630
0.9028	High Similarity	NPC319647
0.9028	High Similarity	NPC471388
0.9028	High Similarity	NPC25966
0.9021	High Similarity	NPC269091
0.9021	High Similarity	NPC265433
0.9021	High Similarity	NPC306441
0.9021	High Similarity	NPC270456
0.9021	High Similarity	NPC248727
0.9021	High Similarity	NPC16435
0.9021	High Similarity	NPC162659
0.9021	High Similarity	NPC227503
0.9021	High Similarity	NPC470802
0.9021	High Similarity	NPC302701
0.9021	High Similarity	NPC474639
0.9021	High Similarity	NPC230734
0.9021	High Similarity	NPC472800
0.8986	High Similarity	NPC112251
0.8973	High Similarity	NPC107161
0.8966	High Similarity	NPC291101
0.8966	High Similarity	NPC309124
0.8966	High Similarity	NPC234568
0.8966	High Similarity	NPC266197
0.8966	High Similarity	NPC184797
0.8958	High Similarity	NPC211549
0.8958	High Similarity	NPC102904
0.8958	High Similarity	NPC176051
0.8958	High Similarity	NPC326797
0.8958	High Similarity	NPC103976
0.8958	High Similarity	NPC107551
0.8958	High Similarity	NPC276490
0.8958	High Similarity	NPC474282
0.8951	High Similarity	NPC473413
0.8951	High Similarity	NPC474206
0.8951	High Similarity	NPC61946
0.8951	High Similarity	NPC121812
0.8951	High Similarity	NPC260898
0.8951	High Similarity	NPC94750
0.8951	High Similarity	NPC164787
0.8951	High Similarity	NPC112246
0.8951	High Similarity	NPC151224
0.8951	High Similarity	NPC47398
0.8951	High Similarity	NPC112939
0.8951	High Similarity	NPC470356
0.8951	High Similarity	NPC234333
0.8926	High Similarity	NPC58190
0.8926	High Similarity	NPC18185
0.8926	High Similarity	NPC262911
0.8926	High Similarity	NPC294558
0.8926	High Similarity	NPC108811
0.8926	High Similarity	NPC170103
0.8926	High Similarity	NPC236202
0.8926	High Similarity	NPC82917
0.8926	High Similarity	NPC70409
0.8926	High Similarity	NPC263940
0.8926	High Similarity	NPC204770
0.8926	High Similarity	NPC202742
0.8919	High Similarity	NPC181615
0.8919	High Similarity	NPC221318
0.8904	High Similarity	NPC247291
0.8904	High Similarity	NPC71046
0.8897	High Similarity	NPC473739
0.8897	High Similarity	NPC236306
0.8897	High Similarity	NPC19869
0.8897	High Similarity	NPC6300
0.8897	High Similarity	NPC230124
0.8897	High Similarity	NPC114171
0.8897	High Similarity	NPC232164
0.8889	High Similarity	NPC472336
0.8889	High Similarity	NPC234952
0.8889	High Similarity	NPC173660
0.8889	High Similarity	NPC68292
0.8889	High Similarity	NPC472334
0.8882	High Similarity	NPC21902
0.8881	High Similarity	NPC478085
0.8881	High Similarity	NPC317380
0.8874	High Similarity	NPC225815
0.8874	High Similarity	NPC185955
0.8874	High Similarity	NPC469706
0.8874	High Similarity	NPC183380
0.8874	High Similarity	NPC218041
0.8874	High Similarity	NPC214326
0.8874	High Similarity	NPC260781
0.8874	High Similarity	NPC9933
0.8874	High Similarity	NPC182368
0.8874	High Similarity	NPC145979
0.8874	High Similarity	NPC469707
0.8867	High Similarity	NPC227516
0.8867	High Similarity	NPC20757
0.8859	High Similarity	NPC324492
0.8859	High Similarity	NPC471608
0.8859	High Similarity	NPC96576
0.8859	High Similarity	NPC317053
0.8844	High Similarity	NPC175838
0.8836	High Similarity	NPC308768
0.8836	High Similarity	NPC73505
0.8836	High Similarity	NPC12668
0.8836	High Similarity	NPC295719
0.8836	High Similarity	NPC34431
0.8836	High Similarity	NPC254759
0.8836	High Similarity	NPC22317
0.8836	High Similarity	NPC160283
0.8836	High Similarity	NPC27495
0.8836	High Similarity	NPC165026
0.8828	High Similarity	NPC56329
0.8828	High Similarity	NPC242715
0.8828	High Similarity	NPC477938
0.8824	High Similarity	NPC78809
0.8819	High Similarity	NPC472337
0.8819	High Similarity	NPC313081
0.8819	High Similarity	NPC256262
0.8819	High Similarity	NPC195022
0.8811	High Similarity	NPC11060
0.8811	High Similarity	NPC475840
0.8811	High Similarity	NPC263064
0.8808	High Similarity	NPC476969
0.8808	High Similarity	NPC44452
0.88	High Similarity	NPC320970
0.88	High Similarity	NPC320671
0.88	High Similarity	NPC328567
0.88	High Similarity	NPC327412
0.8784	High Similarity	NPC469630
0.8784	High Similarity	NPC258083
0.8776	High Similarity	NPC311530
0.8767	High Similarity	NPC218131
0.8767	High Similarity	NPC22517
0.8767	High Similarity	NPC220344
0.8767	High Similarity	NPC105847
0.8767	High Similarity	NPC275061
0.8767	High Similarity	NPC475836
0.8767	High Similarity	NPC292882
0.8767	High Similarity	NPC243996
0.8767	High Similarity	NPC132804
0.8767	High Similarity	NPC212942
0.8767	High Similarity	NPC79622
0.8767	High Similarity	NPC29868
0.8767	High Similarity	NPC243759
0.8766	High Similarity	NPC159922
0.8759	High Similarity	NPC263367
0.8759	High Similarity	NPC30632
0.8759	High Similarity	NPC54743
0.8759	High Similarity	NPC477939
0.8759	High Similarity	NPC209985
0.8759	High Similarity	NPC177160
0.8759	High Similarity	NPC143139
0.8759	High Similarity	NPC327735
0.8759	High Similarity	NPC29799

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 NPC2745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	874
0.2-0.3	1865
0.3-0.4	2728
0.4-0.5	1687
0.5-0.6	904
0.6-0.7	542
0.7-0.8	140
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD1613	Approved
0.8741	High Similarity	NPD1612	Clinical (unspecified phase)
0.8531	High Similarity	NPD3027	Phase 3
0.8472	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD6674	Discontinued
0.8392	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4908	Phase 1
0.8276	Intermediate Similarity	NPD4625	Phase 3
0.8133	Intermediate Similarity	NPD5844	Phase 1
0.8039	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3620	Phase 2
0.7987	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD4749	Approved
0.7972	Intermediate Similarity	NPD1610	Phase 2
0.7964	Intermediate Similarity	NPD7228	Approved
0.795	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2861	Phase 2
0.7888	Intermediate Similarity	NPD1934	Approved
0.7866	Intermediate Similarity	NPD6234	Discontinued
0.7844	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6166	Phase 2
0.7844	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6100	Approved
0.7843	Intermediate Similarity	NPD6099	Approved
0.7778	Intermediate Similarity	NPD37	Approved
0.7759	Intermediate Similarity	NPD4663	Approved
0.775	Intermediate Similarity	NPD1653	Approved
0.7744	Intermediate Similarity	NPD4965	Approved
0.7744	Intermediate Similarity	NPD4966	Approved
0.7744	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4967	Phase 2
0.7714	Intermediate Similarity	NPD7906	Approved
0.7697	Intermediate Similarity	NPD5735	Approved
0.7687	Intermediate Similarity	NPD6696	Suspended
0.7687	Intermediate Similarity	NPD8651	Approved
0.7661	Intermediate Similarity	NPD7074	Phase 3
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4060	Phase 1
0.7622	Intermediate Similarity	NPD2801	Approved
0.7605	Intermediate Similarity	NPD5494	Approved
0.7602	Intermediate Similarity	NPD7054	Approved
0.7588	Intermediate Similarity	NPD7473	Discontinued
0.7586	Intermediate Similarity	NPD4577	Approved
0.7586	Intermediate Similarity	NPD7312	Approved
0.7586	Intermediate Similarity	NPD7311	Approved
0.7586	Intermediate Similarity	NPD4578	Approved
0.7586	Intermediate Similarity	NPD7310	Approved
0.7586	Intermediate Similarity	NPD7313	Approved
0.7582	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5124	Phase 1
0.7569	Intermediate Similarity	NPD1548	Phase 1
0.7562	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7199	Phase 2
0.7558	Intermediate Similarity	NPD7472	Approved
0.7543	Intermediate Similarity	NPD7309	Approved
0.7529	Intermediate Similarity	NPD27	Approved
0.7529	Intermediate Similarity	NPD2489	Approved
0.7515	Intermediate Similarity	NPD3051	Approved
0.7515	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7240	Approved
0.7471	Intermediate Similarity	NPD2970	Approved
0.7471	Intermediate Similarity	NPD2969	Approved
0.747	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD8127	Discontinued
0.7456	Intermediate Similarity	NPD6959	Discontinued
0.7453	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4380	Phase 2
0.7429	Intermediate Similarity	NPD7549	Discontinued
0.7417	Intermediate Similarity	NPD3018	Phase 2
0.7383	Intermediate Similarity	NPD5327	Phase 3
0.7372	Intermediate Similarity	NPD4536	Approved
0.7372	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4538	Approved
0.7371	Intermediate Similarity	NPD7251	Discontinued
0.7368	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6671	Approved
0.7361	Intermediate Similarity	NPD7157	Approved
0.7346	Intermediate Similarity	NPD7447	Phase 1
0.7345	Intermediate Similarity	NPD8054	Approved
0.7345	Intermediate Similarity	NPD8053	Approved
0.7343	Intermediate Similarity	NPD5283	Phase 1
0.7342	Intermediate Similarity	NPD5762	Approved
0.7342	Intermediate Similarity	NPD5763	Approved
0.7342	Intermediate Similarity	NPD7266	Discontinued
0.7341	Intermediate Similarity	NPD3818	Discontinued
0.733	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7808	Phase 3
0.7321	Intermediate Similarity	NPD3882	Suspended
0.732	Intermediate Similarity	NPD7095	Approved
0.7314	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6797	Phase 2
0.731	Intermediate Similarity	NPD7340	Approved
0.731	Intermediate Similarity	NPD3787	Discontinued
0.7308	Intermediate Similarity	NPD4097	Suspended
0.7308	Intermediate Similarity	NPD6353	Approved
0.7305	Intermediate Similarity	NPD1465	Phase 2
0.729	Intermediate Similarity	NPD4140	Approved
0.7285	Intermediate Similarity	NPD3094	Phase 2
0.7284	Intermediate Similarity	NPD1511	Approved
0.7284	Intermediate Similarity	NPD7213	Phase 3
0.7284	Intermediate Similarity	NPD7212	Phase 2
0.7278	Intermediate Similarity	NPD7075	Discontinued
0.7278	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6559	Discontinued
0.7267	Intermediate Similarity	NPD2983	Phase 2
0.7267	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2982	Phase 2
0.7248	Intermediate Similarity	NPD1091	Approved
0.7233	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5058	Phase 3
0.7215	Intermediate Similarity	NPD5588	Approved
0.7215	Intermediate Similarity	NPD5960	Phase 3
0.7205	Intermediate Similarity	NPD4628	Phase 3
0.7205	Intermediate Similarity	NPD7466	Approved
0.7203	Intermediate Similarity	NPD228	Approved
0.7202	Intermediate Similarity	NPD8455	Phase 2
0.7202	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5929	Approved
0.7202	Intermediate Similarity	NPD7819	Suspended
0.72	Intermediate Similarity	NPD2981	Phase 2
0.72	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1512	Approved
0.7186	Intermediate Similarity	NPD6072	Discontinued
0.7186	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7041	Phase 2
0.7178	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7833	Phase 2
0.7176	Intermediate Similarity	NPD7831	Phase 2
0.7176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3817	Phase 2
0.7152	Intermediate Similarity	NPD7097	Phase 1
0.7151	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD5177	Phase 3
0.7134	Intermediate Similarity	NPD3657	Discovery
0.7134	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3092	Approved
0.7118	Intermediate Similarity	NPD7768	Phase 2
0.7117	Intermediate Similarity	NPD7124	Phase 2
0.711	Intermediate Similarity	NPD7229	Phase 3
0.711	Intermediate Similarity	NPD6071	Discontinued
0.7107	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1398	Phase 1
0.7099	Intermediate Similarity	NPD8166	Discontinued
0.7099	Intermediate Similarity	NPD3892	Phase 2
0.7099	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4110	Phase 3
0.7099	Intermediate Similarity	NPD6331	Phase 2
0.7095	Intermediate Similarity	NPD7741	Discontinued
0.7095	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD8313	Approved
0.7091	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7680	Approved
0.7081	Intermediate Similarity	NPD2424	Discontinued
0.7074	Intermediate Similarity	NPD2493	Approved
0.7074	Intermediate Similarity	NPD2494	Approved
0.707	Intermediate Similarity	NPD1558	Phase 1
0.707	Intermediate Similarity	NPD2238	Phase 2
0.7066	Intermediate Similarity	NPD4005	Discontinued
0.7063	Intermediate Similarity	NPD3022	Approved
0.7063	Intermediate Similarity	NPD3021	Approved
0.7059	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2563	Approved
0.7059	Intermediate Similarity	NPD2560	Approved
0.7056	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2677	Approved
0.7055	Intermediate Similarity	NPD6190	Approved
0.7055	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4582	Approved
0.7053	Intermediate Similarity	NPD4583	Approved
0.7051	Intermediate Similarity	NPD7985	Registered
0.7039	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7843	Approved
0.703	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6355	Discontinued
0.7024	Intermediate Similarity	NPD4675	Approved
0.7024	Intermediate Similarity	NPD6599	Discontinued
0.7024	Intermediate Similarity	NPD4678	Approved
0.702	Intermediate Similarity	NPD3705	Approved
0.7019	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4624	Approved
0.7006	Intermediate Similarity	NPD8156	Discontinued
0.7	Intermediate Similarity	NPD5126	Approved
0.7	Intermediate Similarity	NPD4004	Approved
0.7	Intermediate Similarity	NPD5125	Phase 3
0.7	Intermediate Similarity	NPD4002	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data