NPASS Compound

Structure

CID195561 OpenBabel06191715582D 34 37 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 0.8660 -2.5000 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 -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 -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 -1.5000 0.0000 C 0 0 2 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 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 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 17 1 0 0 0 0 2 17 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 17 2 0 0 0 0 7 8 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 26 1 0 0 0 0 11 29 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 19 2 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 23 2 0 0 0 0 15 18 1 0 0 0 0 15 24 2 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 20 27 2 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 27 1 0 0 0 0 24 32 1 0 0 0 0 25 28 1 0 0 0 0 25 29 1 1 0 0 0 26 28 1 0 0 0 0 26 33 1 1 0 0 0 27 34 1 0 0 0 0 29 5 1 1 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.26
Volume:	498.774
LogP:	6.102
LogD:	4.051
LogS:	-3.039
# Rotatable Bonds:	4
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	4.228
Fsp3:	0.448
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.229
MDCK Permeability:	1.2146194421802647e-05
Pgp-inhibitor:	0.938
Pgp-substrate:	0.475
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	100.08806610107422%
Volume Distribution (VD):	1.064
Pgp-substrate:	1.1806129217147827%

ADMET: Metabolism

CYP1A2-inhibitor:	0.786
CYP1A2-substrate:	0.277
CYP2C19-inhibitor:	0.759
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.529
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.601
CYP2D6-substrate:	0.314
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	7.485
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.666
Human Hepatotoxicity (H-HT):	0.567
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.939
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.854
Respiratory Toxicity:	0.841

Download Data

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

Natural Product: NPC195561

Natural Product ID:	NPC195561
*Common Name:**	Schweinfurthin G
IUPAC Name:	(2R,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-2,5-diol
Synonyms:	Schweinfurthin G
Standard InCHIKey:	CGJIPMVTBQUUQL-GEDZTWKOSA-N
Standard InCHI:	InChI=1S/C29H36O5/c1-17(2)6-9-21-22(30)13-19(14-23(21)31)8-7-18-12-20-16-25-28(3,4)26(33)10-11-29(25,5)34-27(20)24(32)15-18/h6-8,12-15,25-26,30-33H,9-11,16H2,1-5H3/b8-7+/t25-,26-,29-/m1/s1
SMILES:	CC(=CCc1c(cc(/C=C/c2cc3C[C@@H]4C(C)(C)[C@@H](CC[C@@]4(C)Oc3c(c2)O)O)cc1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL223142
PubChem CID:	16116603
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	leaves	Krachong waterfall area, Trang Province, Thailand	2001-APR	PMID[15974621]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	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	n.a.	leaf	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	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]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11884	Macaranga tanarius	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	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	390.0	nM	PMID[525543]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	=	10.0	nM	PMID[525544]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	800.0	nM	PMID[525545]
NPT1535	Cell Line	U-87 MG	Homo sapiens	EC50	=	45.0	nM	PMID[525545]

☑ 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 NPC195561 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	498
0.1-0.2	1532
0.2-0.3	3718
0.3-0.4	8941
0.4-0.5	9730
0.5-0.6	4134
0.6-0.7	7604
0.7-0.8	5370
0.8-0.85	847
0.85-0.9	284
0.9-0.95	31
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC2745
0.9861	High Similarity	NPC157783
0.986	High Similarity	NPC158784
0.9859	High Similarity	NPC212142
0.9792	High Similarity	NPC302915
0.9724	High Similarity	NPC325860
0.9448	High Similarity	NPC473876
0.9379	High Similarity	NPC474397
0.9375	High Similarity	NPC90645
0.9375	High Similarity	NPC472457
0.9324	High Similarity	NPC160196
0.931	High Similarity	NPC233980
0.9306	High Similarity	NPC473845
0.9231	High Similarity	NPC35216
0.92	High Similarity	NPC80918
0.92	High Similarity	NPC188578
0.9172	High Similarity	NPC473108
0.9172	High Similarity	NPC50250
0.9167	High Similarity	NPC2613
0.9167	High Similarity	NPC475891
0.9167	High Similarity	NPC204347
0.9167	High Similarity	NPC59841
0.9167	High Similarity	NPC323126
0.9161	High Similarity	NPC198038
0.9116	High Similarity	NPC16269
0.9116	High Similarity	NPC21776
0.9116	High Similarity	NPC101376
0.911	High Similarity	NPC469557
0.9103	High Similarity	NPC474104
0.9097	High Similarity	NPC471389
0.9097	High Similarity	NPC265075
0.9091	High Similarity	NPC260741
0.9091	High Similarity	NPC70682
0.906	High Similarity	NPC477612
0.9048	High Similarity	NPC260397
0.9041	High Similarity	NPC469795
0.9041	High Similarity	NPC45257
0.9041	High Similarity	NPC63879
0.9041	High Similarity	NPC93323
0.9041	High Similarity	NPC12641
0.9041	High Similarity	NPC280092
0.9028	High Similarity	NPC234568
0.9028	High Similarity	NPC259519
0.8993	High Similarity	NPC211561
0.8973	High Similarity	NPC102044
0.8973	High Similarity	NPC85264
0.8973	High Similarity	NPC47633
0.8973	High Similarity	NPC477616
0.8966	High Similarity	NPC87725
0.8966	High Similarity	NPC178054
0.8966	High Similarity	NPC263261
0.8958	High Similarity	NPC245207
0.8958	High Similarity	NPC471388
0.8958	High Similarity	NPC127218
0.8958	High Similarity	NPC319647
0.8958	High Similarity	NPC184613
0.8958	High Similarity	NPC32630
0.8958	High Similarity	NPC25966
0.8951	High Similarity	NPC248727
0.8951	High Similarity	NPC162659
0.8951	High Similarity	NPC227503
0.8951	High Similarity	NPC302701
0.8951	High Similarity	NPC230734
0.8951	High Similarity	NPC470802
0.8951	High Similarity	NPC306441
0.8951	High Similarity	NPC265433
0.8951	High Similarity	NPC269091
0.8951	High Similarity	NPC472800
0.8951	High Similarity	NPC16435
0.8951	High Similarity	NPC270456
0.8951	High Similarity	NPC474639
0.8919	High Similarity	NPC112251
0.8904	High Similarity	NPC107161
0.8897	High Similarity	NPC184797
0.8897	High Similarity	NPC291101
0.8897	High Similarity	NPC309124
0.8897	High Similarity	NPC266197
0.8889	High Similarity	NPC276490
0.8889	High Similarity	NPC474282
0.8889	High Similarity	NPC211549
0.8889	High Similarity	NPC326797
0.8889	High Similarity	NPC103976
0.8889	High Similarity	NPC102904
0.8889	High Similarity	NPC107551
0.8889	High Similarity	NPC176051
0.8881	High Similarity	NPC164787
0.8881	High Similarity	NPC474206
0.8881	High Similarity	NPC112246
0.8881	High Similarity	NPC121812
0.8881	High Similarity	NPC151224
0.8881	High Similarity	NPC470356
0.8881	High Similarity	NPC94750
0.8881	High Similarity	NPC234333
0.8881	High Similarity	NPC61946
0.8881	High Similarity	NPC260898
0.8881	High Similarity	NPC473413
0.8881	High Similarity	NPC112939
0.8881	High Similarity	NPC47398
0.8859	High Similarity	NPC170103
0.8859	High Similarity	NPC108811
0.8859	High Similarity	NPC236202
0.8859	High Similarity	NPC202742
0.8859	High Similarity	NPC82917
0.8859	High Similarity	NPC204770
0.8859	High Similarity	NPC263940
0.8859	High Similarity	NPC70409
0.8859	High Similarity	NPC18185
0.8859	High Similarity	NPC58190
0.8859	High Similarity	NPC262911
0.8859	High Similarity	NPC294558
0.8851	High Similarity	NPC181615
0.8851	High Similarity	NPC221318
0.8836	High Similarity	NPC71046
0.8836	High Similarity	NPC247291
0.8828	High Similarity	NPC232164
0.8828	High Similarity	NPC473739
0.8828	High Similarity	NPC6300
0.8828	High Similarity	NPC230124
0.8828	High Similarity	NPC236306
0.8828	High Similarity	NPC114171
0.8828	High Similarity	NPC19869
0.8819	High Similarity	NPC173660
0.8819	High Similarity	NPC472334
0.8819	High Similarity	NPC68292
0.8819	High Similarity	NPC472336
0.8819	High Similarity	NPC234952
0.8816	High Similarity	NPC21902
0.8811	High Similarity	NPC317380
0.8811	High Similarity	NPC478085
0.8808	High Similarity	NPC183380
0.8808	High Similarity	NPC469706
0.8808	High Similarity	NPC260781
0.8808	High Similarity	NPC218041
0.8808	High Similarity	NPC182368
0.8808	High Similarity	NPC145979
0.8808	High Similarity	NPC9933
0.8808	High Similarity	NPC469707
0.8808	High Similarity	NPC225815
0.8808	High Similarity	NPC185955
0.8808	High Similarity	NPC214326
0.88	High Similarity	NPC227516
0.88	High Similarity	NPC20757
0.8792	High Similarity	NPC324492
0.8792	High Similarity	NPC96576
0.8792	High Similarity	NPC471608
0.8792	High Similarity	NPC317053
0.8776	High Similarity	NPC175838
0.8767	High Similarity	NPC160283
0.8767	High Similarity	NPC34431
0.8767	High Similarity	NPC73505
0.8767	High Similarity	NPC308768
0.8767	High Similarity	NPC295719
0.8767	High Similarity	NPC254759
0.8767	High Similarity	NPC27495
0.8767	High Similarity	NPC165026
0.8767	High Similarity	NPC12668
0.8767	High Similarity	NPC22317
0.8759	High Similarity	NPC242715
0.8759	High Similarity	NPC477938
0.8759	High Similarity	NPC56329
0.8758	High Similarity	NPC78809
0.875	High Similarity	NPC313081
0.875	High Similarity	NPC472337
0.875	High Similarity	NPC256262
0.875	High Similarity	NPC195022
0.8742	High Similarity	NPC476969
0.8742	High Similarity	NPC44452
0.8741	High Similarity	NPC263064
0.8741	High Similarity	NPC227719
0.8741	High Similarity	NPC11060
0.8741	High Similarity	NPC475840
0.8733	High Similarity	NPC327412
0.8733	High Similarity	NPC320970
0.8733	High Similarity	NPC328567
0.8733	High Similarity	NPC320671
0.8716	High Similarity	NPC469630
0.8716	High Similarity	NPC258083
0.8707	High Similarity	NPC311530
0.8701	High Similarity	NPC159922
0.8699	High Similarity	NPC212942
0.8699	High Similarity	NPC243996
0.8699	High Similarity	NPC220344
0.8699	High Similarity	NPC29868
0.8699	High Similarity	NPC132804
0.8699	High Similarity	NPC22517
0.8699	High Similarity	NPC218131
0.8699	High Similarity	NPC243759
0.8699	High Similarity	NPC292882
0.8699	High Similarity	NPC475836
0.8699	High Similarity	NPC105847
0.8699	High Similarity	NPC275061
0.8699	High Similarity	NPC79622
0.8693	High Similarity	NPC226809
0.8693	High Similarity	NPC279406
0.869	High Similarity	NPC300846
0.869	High Similarity	NPC263367
0.869	High Similarity	NPC126101
0.869	High Similarity	NPC143139
0.869	High Similarity	NPC476639
0.869	High Similarity	NPC477939

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 NPC195561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	867
0.2-0.3	1844
0.3-0.4	2720
0.4-0.5	1716
0.5-0.6	904
0.6-0.7	568
0.7-0.8	126
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8671	High Similarity	NPD1613	Approved
0.8671	High Similarity	NPD1612	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3027	Phase 3
0.8403	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6674	Discontinued
0.8322	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD4908	Phase 1
0.8207	Intermediate Similarity	NPD4625	Phase 3
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8041	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3620	Phase 2
0.7974	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4749	Approved
0.7904	Intermediate Similarity	NPD7228	Approved
0.7902	Intermediate Similarity	NPD1610	Phase 2
0.7888	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1934	Approved
0.7823	Intermediate Similarity	NPD2861	Phase 2
0.7805	Intermediate Similarity	NPD6234	Discontinued
0.7784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6166	Phase 2
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6099	Approved
0.7748	Intermediate Similarity	NPD5735	Approved
0.7716	Intermediate Similarity	NPD37	Approved
0.7701	Intermediate Similarity	NPD4663	Approved
0.7688	Intermediate Similarity	NPD1653	Approved
0.7683	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4967	Phase 2
0.7683	Intermediate Similarity	NPD4966	Approved
0.7683	Intermediate Similarity	NPD4965	Approved
0.7682	Intermediate Similarity	NPD4060	Phase 1
0.7657	Intermediate Similarity	NPD7906	Approved
0.7619	Intermediate Similarity	NPD8651	Approved
0.7619	Intermediate Similarity	NPD6696	Suspended
0.7602	Intermediate Similarity	NPD7074	Phase 3
0.758	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD27	Approved
0.7574	Intermediate Similarity	NPD2489	Approved
0.7561	Intermediate Similarity	NPD2801	Approved
0.7545	Intermediate Similarity	NPD5494	Approved
0.7544	Intermediate Similarity	NPD7054	Approved
0.7529	Intermediate Similarity	NPD7473	Discontinued
0.7529	Intermediate Similarity	NPD4578	Approved
0.7529	Intermediate Similarity	NPD7310	Approved
0.7529	Intermediate Similarity	NPD7311	Approved
0.7529	Intermediate Similarity	NPD7312	Approved
0.7529	Intermediate Similarity	NPD7313	Approved
0.7529	Intermediate Similarity	NPD4577	Approved
0.7516	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8127	Discontinued
0.75	Intermediate Similarity	NPD7472	Approved
0.7486	Intermediate Similarity	NPD7309	Approved
0.7456	Intermediate Similarity	NPD6232	Discontinued
0.7456	Intermediate Similarity	NPD3051	Approved
0.7443	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5327	Phase 3
0.7419	Intermediate Similarity	NPD4538	Approved
0.7419	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4536	Approved
0.7414	Intermediate Similarity	NPD7240	Approved
0.7413	Intermediate Similarity	NPD6671	Approved
0.7413	Intermediate Similarity	NPD7157	Approved
0.7412	Intermediate Similarity	NPD2969	Approved
0.7412	Intermediate Similarity	NPD2970	Approved
0.741	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6959	Discontinued
0.7394	Intermediate Similarity	NPD5283	Phase 1
0.7391	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5763	Approved
0.7389	Intermediate Similarity	NPD5762	Approved
0.7378	Intermediate Similarity	NPD4380	Phase 2
0.7371	Intermediate Similarity	NPD7549	Discontinued
0.7368	Intermediate Similarity	NPD7095	Approved
0.7361	Intermediate Similarity	NPD7340	Approved
0.7355	Intermediate Similarity	NPD6353	Approved
0.7355	Intermediate Similarity	NPD4097	Suspended
0.7351	Intermediate Similarity	NPD3018	Phase 2
0.7338	Intermediate Similarity	NPD4140	Approved
0.7333	Intermediate Similarity	NPD3094	Phase 2
0.7315	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7251	Discontinued
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8054	Approved
0.7288	Intermediate Similarity	NPD8053	Approved
0.7284	Intermediate Similarity	NPD7447	Phase 1
0.7283	Intermediate Similarity	NPD3818	Discontinued
0.7278	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3882	Suspended
0.7261	Intermediate Similarity	NPD5588	Approved
0.7261	Intermediate Similarity	NPD5960	Phase 3
0.7257	Intermediate Similarity	NPD6797	Phase 2
0.7257	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD228	Approved
0.7251	Intermediate Similarity	NPD3787	Discontinued
0.7246	Intermediate Similarity	NPD5929	Approved
0.7246	Intermediate Similarity	NPD1465	Phase 2
0.7222	Intermediate Similarity	NPD1511	Approved
0.7222	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7212	Phase 2
0.7222	Intermediate Similarity	NPD7041	Phase 2
0.7222	Intermediate Similarity	NPD7213	Phase 3
0.7219	Intermediate Similarity	NPD7831	Phase 2
0.7219	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7075	Discontinued
0.7219	Intermediate Similarity	NPD7833	Phase 2
0.7216	Intermediate Similarity	NPD6559	Discontinued
0.7212	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2983	Phase 2
0.72	Intermediate Similarity	NPD2982	Phase 2
0.7197	Intermediate Similarity	NPD7097	Phase 1
0.7188	Intermediate Similarity	NPD5177	Phase 3
0.7181	Intermediate Similarity	NPD1091	Approved
0.7181	Intermediate Similarity	NPD3092	Approved
0.7179	Intermediate Similarity	NPD3657	Discovery
0.717	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5058	Phase 3
0.7153	Intermediate Similarity	NPD1398	Phase 1
0.7152	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD7466	Approved
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7143	Intermediate Similarity	NPD6331	Phase 2
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1512	Approved
0.7133	Intermediate Similarity	NPD2981	Phase 2
0.7127	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6072	Discontinued
0.7126	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2424	Discontinued
0.7118	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2238	Phase 2
0.7113	Intermediate Similarity	NPD3022	Approved
0.7113	Intermediate Similarity	NPD3021	Approved
0.7101	Intermediate Similarity	NPD3817	Phase 2
0.7097	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7985	Registered
0.7097	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3751	Discontinued
0.7086	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7843	Approved
0.7081	Intermediate Similarity	NPD1652	Phase 2
0.7073	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7059	Intermediate Similarity	NPD4624	Approved
0.7059	Intermediate Similarity	NPD7768	Phase 2
0.7055	Intermediate Similarity	NPD7124	Phase 2
0.7052	Intermediate Similarity	NPD6071	Discontinued
0.7052	Intermediate Similarity	NPD7229	Phase 3
0.7049	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2684	Approved
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7037	Intermediate Similarity	NPD7680	Approved
0.7037	Intermediate Similarity	NPD3892	Phase 2
0.7035	Intermediate Similarity	NPD4666	Phase 3
0.703	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3091	Approved
0.7027	Intermediate Similarity	NPD7741	Discontinued
0.7021	Intermediate Similarity	NPD2494	Approved
0.7021	Intermediate Similarity	NPD2493	Approved
0.7006	Intermediate Similarity	NPD1558	Phase 1
0.7006	Intermediate Similarity	NPD4005	Discontinued
0.7	Intermediate Similarity	NPD4582	Approved
0.7	Intermediate Similarity	NPD2563	Approved
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2560	Approved
0.7	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4583	Approved
0.6995	Remote Similarity	NPD2488	Approved
0.6995	Remote Similarity	NPD2490	Approved
0.6994	Remote Similarity	NPD6190	Approved
0.6994	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2677	Approved
0.6993	Remote Similarity	NPD4750	Phase 3
0.6987	Remote Similarity	NPD7294	Phase 1
0.6987	Remote Similarity	NPD6798	Discontinued
0.6982	Remote Similarity	NPD5722	Discontinued
0.698	Remote Similarity	NPD1357	Approved
0.6977	Remote Similarity	NPD5709	Phase 3
0.6972	Remote Similarity	NPD290	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