NPASS Compound

Structure

NPC229348 OpenBabel07101718222D 34 38 0 0 1 0 0 0 0 0999 V2000 0.3717 4.2036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8954 0.5899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1309 1.5066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9970 1.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2649 1.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9970 0.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4176 2.8717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5436 -0.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2819 3.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9285 -1.5761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5873 -0.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4762 3.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4750 1.4973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5218 -0.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2649 0.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3745 2.6834 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1309 -0.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 -1.1977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9620 2.3707 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7408 1.9254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4939 1.6905 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1835 -2.1488 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 6.9230 -1.4715 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8963 -0.9898 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9549 2.4901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7336 1.8060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1616 -2.3567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5144 -2.8920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 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 12 2 0 0 0 0 2 13 2 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 2 0 0 0 0 6 18 2 0 0 0 0 7 12 1 0 0 0 0 7 21 1 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 15 18 1 0 0 0 0 16 9 1 1 0 0 0 16 22 1 0 0 0 0 17 11 1 6 0 0 0 17 23 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 8 1 1 0 0 0 19 25 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 1 0 0 0 21 23 1 0 0 0 0 21 30 1 6 0 0 0 22 13 1 1 0 0 0 22 24 1 0 0 0 0 23 24 1 0 0 0 0 24 34 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.21
Volume:	469.113
LogP:	0.21
LogD:	1.067
LogS:	-2.788
# Rotatable Bonds:	6
TPSA:	131.88
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	4.765
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.072
MDCK Permeability:	3.1560341540171066e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.876

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	51.65005874633789%
Volume Distribution (VD):	0.567
Pgp-substrate:	54.94573211669922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.33
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.239
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	3.9
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.436
Human Hepatotoxicity (H-HT):	0.986
Drug-inuced Liver Injury (DILI):	0.71
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.703
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.07
Carcinogencity:	0.072
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC229348

Natural Product ID:	NPC229348
*Common Name:**	Pulchellamine F
IUPAC Name:	(2S)-2-[[(3R,3aR,4S,6aR,8S,9aR,9bR)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-3-yl]methylamino]-3-(1H-indol-3-yl)propanoic acid
Synonyms:	Pulchellamine F
Standard InCHIKey:	RSGXFKJWMJPECM-XQQBHHJWSA-N
Standard InCHI:	InChI=1S/C26H30N2O6/c1-12-7-21(30)23-17(26(33)34-24(23)22-13(2)20(29)9-16(12)22)11-28-19(25(31)32)8-14-10-27-18-6-4-3-5-15(14)18/h3-6,10,16-17,19-24,27-30H,1-2,7-9,11H2,(H,31,32)/t16-,17-,19-,20-,21-,22-,23+,24+/m0/s1
SMILES:	C=C1C[C@@H]([C@H]2[C@H](CN[C@@H](Cc3c[nH]c4ccccc34)C(=O)O)C(=O)O[C@@H]2[C@H]2C(=C)[C@H](C[C@@H]12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516867
PubChem CID:	24862016
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[18314958]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	uM	PMID[514291]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	24.19	uM	PMID[514291]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	18.56	uM	PMID[514291]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	30.0	uM	PMID[514291]

☑ 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 NPC229348 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	323
0.1-0.2	1578
0.2-0.3	8900
0.3-0.4	22824
0.4-0.5	4399
0.5-0.6	2713
0.6-0.7	1562
0.7-0.8	391
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8492	Intermediate Similarity	NPC476874
0.8413	Intermediate Similarity	NPC283219
0.8342	Intermediate Similarity	NPC235684
0.8316	Intermediate Similarity	NPC248041
0.8316	Intermediate Similarity	NPC126709
0.8254	Intermediate Similarity	NPC149155
0.8254	Intermediate Similarity	NPC203468
0.8254	Intermediate Similarity	NPC110500
0.8244	Intermediate Similarity	NPC478158
0.8229	Intermediate Similarity	NPC71037
0.8221	Intermediate Similarity	NPC313640
0.8211	Intermediate Similarity	NPC267885
0.819	Intermediate Similarity	NPC281049
0.8173	Intermediate Similarity	NPC54744
0.8168	Intermediate Similarity	NPC84827
0.8168	Intermediate Similarity	NPC14113
0.8168	Intermediate Similarity	NPC145885
0.8163	Intermediate Similarity	NPC321708
0.8154	Intermediate Similarity	NPC315555
0.8134	Intermediate Similarity	NPC478157
0.8128	Intermediate Similarity	NPC193761
0.8084	Intermediate Similarity	NPC64216
0.8073	Intermediate Similarity	NPC89987
0.8069	Intermediate Similarity	NPC293917
0.8068	Intermediate Similarity	NPC469743
0.8042	Intermediate Similarity	NPC78020
0.803	Intermediate Similarity	NPC214428
0.8009	Intermediate Similarity	NPC472762
0.7981	Intermediate Similarity	NPC162860
0.7972	Intermediate Similarity	NPC472285
0.7952	Intermediate Similarity	NPC75634
0.7951	Intermediate Similarity	NPC155143
0.7902	Intermediate Similarity	NPC475506
0.7887	Intermediate Similarity	NPC111275
0.7885	Intermediate Similarity	NPC54420
0.7874	Intermediate Similarity	NPC473376
0.7873	Intermediate Similarity	NPC70155
0.7854	Intermediate Similarity	NPC45459
0.7854	Intermediate Similarity	NPC315491
0.7846	Intermediate Similarity	NPC55772
0.7844	Intermediate Similarity	NPC24370
0.7844	Intermediate Similarity	NPC319232
0.7843	Intermediate Similarity	NPC171317
0.7837	Intermediate Similarity	NPC277350
0.7824	Intermediate Similarity	NPC2395
0.782	Intermediate Similarity	NPC82370
0.782	Intermediate Similarity	NPC320968
0.7817	Intermediate Similarity	NPC469358
0.781	Intermediate Similarity	NPC107077
0.781	Intermediate Similarity	NPC223791
0.7805	Intermediate Similarity	NPC100321
0.78	Intermediate Similarity	NPC213629
0.7798	Intermediate Similarity	NPC235885
0.7794	Intermediate Similarity	NPC262898
0.7783	Intermediate Similarity	NPC475778
0.7773	Intermediate Similarity	NPC234999
0.7756	Intermediate Similarity	NPC473640
0.7756	Intermediate Similarity	NPC149708
0.7755	Intermediate Similarity	NPC213468
0.7752	Intermediate Similarity	NPC475271
0.775	Intermediate Similarity	NPC17059
0.7746	Intermediate Similarity	NPC472291
0.7745	Intermediate Similarity	NPC179701
0.7732	Intermediate Similarity	NPC314603
0.7727	Intermediate Similarity	NPC57690
0.7714	Intermediate Similarity	NPC88008
0.7714	Intermediate Similarity	NPC323927
0.7708	Intermediate Similarity	NPC160105
0.7708	Intermediate Similarity	NPC54988
0.7707	Intermediate Similarity	NPC156704
0.7704	Intermediate Similarity	NPC217372
0.7704	Intermediate Similarity	NPC15573
0.7704	Intermediate Similarity	NPC183662
0.77	Intermediate Similarity	NPC151976
0.77	Intermediate Similarity	NPC207020
0.77	Intermediate Similarity	NPC87856
0.7696	Intermediate Similarity	NPC311276
0.7692	Intermediate Similarity	NPC476073
0.7678	Intermediate Similarity	NPC127677
0.7678	Intermediate Similarity	NPC258062
0.7674	Intermediate Similarity	NPC204491
0.7674	Intermediate Similarity	NPC203614
0.7674	Intermediate Similarity	NPC132211
0.7674	Intermediate Similarity	NPC476114
0.767	Intermediate Similarity	NPC67288
0.7665	Intermediate Similarity	NPC219336
0.7664	Intermediate Similarity	NPC267965
0.7656	Intermediate Similarity	NPC98715
0.765	Intermediate Similarity	NPC280290
0.7647	Intermediate Similarity	NPC267343
0.7644	Intermediate Similarity	NPC300183
0.7636	Intermediate Similarity	NPC125597
0.7634	Intermediate Similarity	NPC323752
0.7633	Intermediate Similarity	NPC241024
0.763	Intermediate Similarity	NPC46225
0.763	Intermediate Similarity	NPC225821
0.7626	Intermediate Similarity	NPC469896
0.7617	Intermediate Similarity	NPC49954
0.7617	Intermediate Similarity	NPC474561
0.7613	Intermediate Similarity	NPC33949
0.7602	Intermediate Similarity	NPC267926
0.76	Intermediate Similarity	NPC228835
0.7598	Intermediate Similarity	NPC55493
0.7596	Intermediate Similarity	NPC470497
0.7593	Intermediate Similarity	NPC36405
0.7591	Intermediate Similarity	NPC147446
0.7591	Intermediate Similarity	NPC266192
0.7588	Intermediate Similarity	NPC233936
0.7586	Intermediate Similarity	NPC154339
0.7585	Intermediate Similarity	NPC131887
0.758	Intermediate Similarity	NPC473317
0.7579	Intermediate Similarity	NPC469762
0.7574	Intermediate Similarity	NPC278434
0.7571	Intermediate Similarity	NPC476115
0.7562	Intermediate Similarity	NPC62510
0.7559	Intermediate Similarity	NPC271862
0.7557	Intermediate Similarity	NPC141428
0.7546	Intermediate Similarity	NPC474412
0.7545	Intermediate Similarity	NPC290529
0.7539	Intermediate Similarity	NPC230869
0.7537	Intermediate Similarity	NPC209917
0.7537	Intermediate Similarity	NPC175474
0.7536	Intermediate Similarity	NPC227582
0.7526	Intermediate Similarity	NPC469785
0.7525	Intermediate Similarity	NPC94752
0.7525	Intermediate Similarity	NPC62749
0.7523	Intermediate Similarity	NPC82070
0.7513	Intermediate Similarity	NPC102423
0.7512	Intermediate Similarity	NPC213308
0.75	Intermediate Similarity	NPC52557
0.75	Intermediate Similarity	NPC279918
0.7489	Intermediate Similarity	NPC314882
0.7487	Intermediate Similarity	NPC63751
0.7476	Intermediate Similarity	NPC474177
0.7475	Intermediate Similarity	NPC188387
0.7475	Intermediate Similarity	NPC163421
0.7467	Intermediate Similarity	NPC474877
0.7464	Intermediate Similarity	NPC74413
0.7461	Intermediate Similarity	NPC282231
0.7456	Intermediate Similarity	NPC15801
0.7441	Intermediate Similarity	NPC474116
0.7437	Intermediate Similarity	NPC59269
0.7432	Intermediate Similarity	NPC229893
0.7429	Intermediate Similarity	NPC79129
0.7429	Intermediate Similarity	NPC249150
0.7429	Intermediate Similarity	NPC49196
0.7429	Intermediate Similarity	NPC195461
0.7429	Intermediate Similarity	NPC252338
0.7429	Intermediate Similarity	NPC81654
0.7429	Intermediate Similarity	NPC313985
0.7424	Intermediate Similarity	NPC478029
0.7423	Intermediate Similarity	NPC40779
0.7422	Intermediate Similarity	NPC477176
0.7422	Intermediate Similarity	NPC470729
0.7422	Intermediate Similarity	NPC326363
0.7419	Intermediate Similarity	NPC234078
0.7419	Intermediate Similarity	NPC221100
0.7416	Intermediate Similarity	NPC470499
0.7416	Intermediate Similarity	NPC50503
0.7415	Intermediate Similarity	NPC329858
0.7415	Intermediate Similarity	NPC83111
0.7415	Intermediate Similarity	NPC95783
0.7415	Intermediate Similarity	NPC314333
0.7412	Intermediate Similarity	NPC478028
0.7409	Intermediate Similarity	NPC52254
0.7409	Intermediate Similarity	NPC74360
0.7409	Intermediate Similarity	NPC131718
0.7404	Intermediate Similarity	NPC11445
0.7402	Intermediate Similarity	NPC317030
0.74	Intermediate Similarity	NPC11126
0.7391	Intermediate Similarity	NPC81802
0.7391	Intermediate Similarity	NPC472210
0.7391	Intermediate Similarity	NPC247735
0.7391	Intermediate Similarity	NPC472295
0.7391	Intermediate Similarity	NPC269886
0.7389	Intermediate Similarity	NPC475969
0.7389	Intermediate Similarity	NPC475859
0.7383	Intermediate Similarity	NPC474905
0.7379	Intermediate Similarity	NPC138370
0.7379	Intermediate Similarity	NPC472097
0.7376	Intermediate Similarity	NPC139291
0.7376	Intermediate Similarity	NPC472108
0.7376	Intermediate Similarity	NPC163055
0.7374	Intermediate Similarity	NPC313791
0.7368	Intermediate Similarity	NPC325976
0.7364	Intermediate Similarity	NPC478006
0.7358	Intermediate Similarity	NPC260900
0.7358	Intermediate Similarity	NPC162730
0.7357	Intermediate Similarity	NPC54803
0.7357	Intermediate Similarity	NPC321592
0.7356	Intermediate Similarity	NPC133366
0.7356	Intermediate Similarity	NPC157828
0.7356	Intermediate Similarity	NPC195239
0.7353	Intermediate Similarity	NPC474707
0.735	Intermediate Similarity	NPC151939
0.7349	Intermediate Similarity	NPC314957
0.7346	Intermediate Similarity	NPC312870
0.7346	Intermediate Similarity	NPC199851
0.7346	Intermediate Similarity	NPC254240
0.7346	Intermediate Similarity	NPC128265

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 NPC229348 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	507
0.2-0.3	779
0.3-0.4	2184
0.4-0.5	3059
0.5-0.6	1888
0.6-0.7	477
0.7-0.8	69
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
0.8474	Intermediate Similarity	NPD2092	Phase 2
0.8474	Intermediate Similarity	NPD2094	Phase 2
0.8474	Intermediate Similarity	NPD2095	Phase 2
0.8429	Intermediate Similarity	NPD2096	Phase 2
0.8429	Intermediate Similarity	NPD2091	Phase 2
0.8254	Intermediate Similarity	NPD482	Approved
0.8115	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8093	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7470	Discontinued
0.8069	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD750	Phase 2
0.7857	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7854	Intermediate Similarity	NPD484	Approved
0.7837	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD8072	Approved
0.7751	Intermediate Similarity	NPD7957	Phase 1
0.7751	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8073	Approved
0.7678	Intermediate Similarity	NPD2509	Approved
0.7678	Intermediate Similarity	NPD2510	Approved
0.7628	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7970	Approved
0.7593	Intermediate Similarity	NPD3393	Approved
0.7593	Intermediate Similarity	NPD3394	Approved
0.7593	Intermediate Similarity	NPD3389	Approved
0.7571	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6595	Phase 3
0.7536	Intermediate Similarity	NPD5426	Phase 3
0.7536	Intermediate Similarity	NPD8272	Phase 2
0.7524	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7001	Phase 3
0.75	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5901	Discontinued
0.7442	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4601	Approved
0.7429	Intermediate Similarity	NPD4600	Approved
0.7415	Intermediate Similarity	NPD4499	Approved
0.7398	Intermediate Similarity	NPD2844	Phase 3
0.7397	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5003	Discontinued
0.7366	Intermediate Similarity	NPD7711	Discontinued
0.7356	Intermediate Similarity	NPD7944	Discontinued
0.735	Intermediate Similarity	NPD2144	Approved
0.7346	Intermediate Similarity	NPD4501	Approved
0.7346	Intermediate Similarity	NPD4500	Approved
0.7327	Intermediate Similarity	NPD3178	Discontinued
0.7327	Intermediate Similarity	NPD3038	Discontinued
0.7321	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8325	Phase 3
0.7318	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8326	Phase 3
0.7311	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD8098	Approved
0.7285	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4427	Phase 2
0.726	Intermediate Similarity	NPD6665	Discontinued
0.7257	Intermediate Similarity	NPD7730	Approved
0.7257	Intermediate Similarity	NPD7731	Approved
0.7251	Intermediate Similarity	NPD7778	Approved
0.7251	Intermediate Similarity	NPD7777	Approved
0.7251	Intermediate Similarity	NPD53	Approved
0.7249	Intermediate Similarity	NPD7953	Approved
0.7249	Intermediate Similarity	NPD7952	Approved
0.7249	Intermediate Similarity	NPD7951	Approved
0.7249	Intermediate Similarity	NPD7790	Approved
0.7249	Intermediate Similarity	NPD7789	Approved
0.7249	Intermediate Similarity	NPD7791	Approved
0.7249	Intermediate Similarity	NPD7950	Approved
0.7244	Intermediate Similarity	NPD7271	Approved
0.7228	Intermediate Similarity	NPD4076	Approved
0.7228	Intermediate Similarity	NPD4079	Approved
0.7225	Intermediate Similarity	NPD7780	Approved
0.7225	Intermediate Similarity	NPD7781	Approved
0.7222	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7824	Approved
0.7192	Intermediate Similarity	NPD5898	Approved
0.7192	Intermediate Similarity	NPD5897	Approved
0.7192	Intermediate Similarity	NPD5899	Approved
0.7178	Intermediate Similarity	NPD3506	Approved
0.7178	Intermediate Similarity	NPD3505	Approved
0.7178	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5065	Approved
0.7163	Intermediate Similarity	NPD2564	Approved
0.7163	Intermediate Similarity	NPD2565	Phase 2
0.7143	Intermediate Similarity	NPD5482	Discontinued
0.7137	Intermediate Similarity	NPD7576	Discontinued
0.7136	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7948	Phase 1
0.7115	Intermediate Similarity	NPD7234	Approved
0.7115	Intermediate Similarity	NPD7233	Approved
0.7112	Intermediate Similarity	NPD3006	Discontinued
0.7089	Intermediate Similarity	NPD7946	Pre-registration
0.7085	Intermediate Similarity	NPD5818	Discontinued
0.7083	Intermediate Similarity	NPD6176	Phase 1
0.7067	Intermediate Similarity	NPD8431	Approved
0.7067	Intermediate Similarity	NPD4948	Discontinued
0.7064	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7603	Discontinued
0.7059	Intermediate Similarity	NPD8096	Phase 3
0.7059	Intermediate Similarity	NPD8097	Phase 3
0.7059	Intermediate Similarity	NPD8093	Discontinued
0.7056	Intermediate Similarity	NPD6999	Discontinued
0.7056	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5596	Phase 2
0.7028	Intermediate Similarity	NPD7618	Phase 3
0.7028	Intermediate Similarity	NPD7619	Phase 3
0.7027	Intermediate Similarity	NPD3794	Approved
0.7027	Intermediate Similarity	NPD3795	Approved
0.7021	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6529	Discontinued
0.6986	Remote Similarity	NPD1392	Approved
0.6986	Remote Similarity	NPD8322	Phase 2
0.6982	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1038	Approved
0.6964	Remote Similarity	NPD5612	Discontinued
0.6957	Remote Similarity	NPD4086	Phase 1
0.6955	Remote Similarity	NPD8423	Phase 2
0.6955	Remote Similarity	NPD8399	Phase 1
0.6951	Remote Similarity	NPD8094	Discontinued
0.6948	Remote Similarity	NPD4602	Approved
0.6944	Remote Similarity	NPD6479	Discontinued
0.6944	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7688	Phase 1
0.6915	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD8289	Discontinued
0.6903	Remote Similarity	NPD7878	Phase 2
0.6897	Remote Similarity	NPD8374	Phase 3
0.6895	Remote Similarity	NPD8283	Approved
0.6895	Remote Similarity	NPD8282	Approved
0.6895	Remote Similarity	NPD56	Approved
0.6895	Remote Similarity	NPD3947	Discontinued
0.6872	Remote Similarity	NPD6770	Approved
0.6867	Remote Similarity	NPD5450	Discontinued
0.6861	Remote Similarity	NPD5475	Discontinued
0.686	Remote Similarity	NPD6452	Discontinued
0.6858	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6995	Phase 1
0.6851	Remote Similarity	NPD8329	Phase 3
0.6849	Remote Similarity	NPD2920	Discontinued
0.6847	Remote Similarity	NPD1326	Approved
0.6847	Remote Similarity	NPD1573	Approved
0.6847	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4506	Discontinued
0.6847	Remote Similarity	NPD1575	Approved
0.6847	Remote Similarity	NPD1325	Approved
0.6842	Remote Similarity	NPD6178	Phase 3
0.6842	Remote Similarity	NPD786	Approved
0.6842	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3961	Discontinued
0.6822	Remote Similarity	NPD802	Phase 2
0.6814	Remote Similarity	NPD8160	Phase 2
0.6812	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7558	Phase 2
0.6808	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6664	Approved
0.6802	Remote Similarity	NPD7665	Phase 2
0.6802	Remote Similarity	NPD7666	Phase 3
0.6798	Remote Similarity	NPD4638	Approved
0.6798	Remote Similarity	NPD4640	Approved
0.6798	Remote Similarity	NPD4639	Approved
0.6796	Remote Similarity	NPD2382	Approved
0.6796	Remote Similarity	NPD2381	Approved
0.6796	Remote Similarity	NPD2380	Approved
0.6786	Remote Similarity	NPD5067	Phase 2
0.6786	Remote Similarity	NPD5066	Phase 2
0.6783	Remote Similarity	NPD8356	Approved
0.678	Remote Similarity	NPD43	Approved
0.678	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6182	Approved
0.6772	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1722	Approved
0.677	Remote Similarity	NPD7707	Approved
0.6769	Remote Similarity	NPD3280	Approved
0.6769	Remote Similarity	NPD1996	Discontinued
0.6763	Remote Similarity	NPD7865	Approved
0.6758	Remote Similarity	NPD7727	Phase 2
0.6756	Remote Similarity	NPD3330	Phase 1
0.6744	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6987	Phase 1
0.6742	Remote Similarity	NPD8114	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