NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.16
Volume:	271.304
LogP:	1.726
LogD:	2.227
LogS:	-2.734
# Rotatable Bonds:	0
TPSA:	39.26
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	3.909
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.803
MDCK Permeability:	8.539786904293578e-06
Pgp-inhibitor:	0.055
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.201
30% Bioavailability (F30%):	0.635

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.848
Plasma Protein Binding (PPB):	53.60700225830078%
Volume Distribution (VD):	2.417
Pgp-substrate:	48.28963088989258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.715
CYP1A2-substrate:	0.656
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.395
CYP2D6-inhibitor:	0.921
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.81

ADMET: Excretion

Clearance (CL):	11.777
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.395
Human Hepatotoxicity (H-HT):	0.671
Drug-inuced Liver Injury (DILI):	0.515
AMES Toxicity:	0.734
Rat Oral Acute Toxicity:	0.871
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.857
Carcinogencity:	0.098
Eye Corrosion:	0.024
Eye Irritation:	0.088
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC95783

Natural Product ID:	NPC95783
*Common Name:**	Fumigaclavine B
IUPAC Name:	(6aR,9R,10S,10aR)-7,9-dimethyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-10-ol
Synonyms:
Standard InCHIKey:	JUXRVSRUBIFVKE-BBDZHYCFSA-N
Standard InCHI:	InChI=1S/C16H20N2O/c1-9-8-18(2)13-6-10-7-17-12-5-3-4-11(14(10)12)15(13)16(9)19/h3-5,7,9,13,15-17,19H,6,8H2,1-2H3/t9-,13-,15-,16+/m1/s1
SMILES:	C[C@@H]1CN(C)[C@@H]2Cc3c[nH]c4cccc(c34)[C@H]2[C@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229125
PubChem CID:	21589072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002679] Ergoline and derivatives [CHEMONTID:0002747] Clavines 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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	>	100.0	ug.mL-1	PMID[537022]

☑ 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 NPC95783 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	408
0.1-0.2	2081
0.2-0.3	14081
0.3-0.4	17969
0.4-0.5	3596
0.5-0.6	2088
0.6-0.7	1649
0.7-0.8	729
0.8-0.85	81
0.85-0.9	13
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC19679
0.9059	High Similarity	NPC37423
0.9059	High Similarity	NPC275305
0.8953	High Similarity	NPC68354
0.8953	High Similarity	NPC151939
0.8902	High Similarity	NPC176199
0.8902	High Similarity	NPC215795
0.8882	High Similarity	NPC194411
0.8837	High Similarity	NPC329688
0.8837	High Similarity	NPC189812
0.8743	High Similarity	NPC300688
0.8713	High Similarity	NPC201700
0.869	High Similarity	NPC56765
0.858	High Similarity	NPC230869
0.8547	High Similarity	NPC474561
0.8547	High Similarity	NPC49954
0.8538	High Similarity	NPC311276
0.8497	Intermediate Similarity	NPC317430
0.8497	Intermediate Similarity	NPC63751
0.8486	Intermediate Similarity	NPC229332
0.8471	Intermediate Similarity	NPC318065
0.8471	Intermediate Similarity	NPC206819
0.8462	Intermediate Similarity	NPC469785
0.8457	Intermediate Similarity	NPC313791
0.8457	Intermediate Similarity	NPC472123
0.8439	Intermediate Similarity	NPC54988
0.8439	Intermediate Similarity	NPC160105
0.8412	Intermediate Similarity	NPC469762
0.8402	Intermediate Similarity	NPC475602
0.838	Intermediate Similarity	NPC233936
0.8372	Intermediate Similarity	NPC282231
0.8352	Intermediate Similarity	NPC314603
0.8343	Intermediate Similarity	NPC259644
0.8343	Intermediate Similarity	NPC469763
0.8343	Intermediate Similarity	NPC25008
0.8343	Intermediate Similarity	NPC469760
0.8343	Intermediate Similarity	NPC469786
0.8343	Intermediate Similarity	NPC469765
0.8343	Intermediate Similarity	NPC73952
0.8333	Intermediate Similarity	NPC139291
0.8333	Intermediate Similarity	NPC472108
0.8324	Intermediate Similarity	NPC194640
0.8324	Intermediate Similarity	NPC40779
0.8314	Intermediate Similarity	NPC279918
0.8297	Intermediate Similarity	NPC474707
0.8294	Intermediate Similarity	NPC80597
0.8294	Intermediate Similarity	NPC212376
0.8294	Intermediate Similarity	NPC75540
0.8294	Intermediate Similarity	NPC211572
0.8294	Intermediate Similarity	NPC70922
0.8256	Intermediate Similarity	NPC41257
0.8251	Intermediate Similarity	NPC317030
0.8251	Intermediate Similarity	NPC204565
0.8242	Intermediate Similarity	NPC188387
0.8242	Intermediate Similarity	NPC163421
0.8238	Intermediate Similarity	NPC314957
0.8232	Intermediate Similarity	NPC472109
0.8232	Intermediate Similarity	NPC472110
0.8226	Intermediate Similarity	NPC474177
0.8218	Intermediate Similarity	NPC102423
0.8218	Intermediate Similarity	NPC90723
0.8212	Intermediate Similarity	NPC59269
0.8207	Intermediate Similarity	NPC65215
0.8207	Intermediate Similarity	NPC173028
0.8198	Intermediate Similarity	NPC286427
0.8182	Intermediate Similarity	NPC154293
0.8142	Intermediate Similarity	NPC15102
0.8136	Intermediate Similarity	NPC280548
0.8132	Intermediate Similarity	NPC163055
0.8131	Intermediate Similarity	NPC251936
0.8118	Intermediate Similarity	NPC33421
0.8103	Intermediate Similarity	NPC215584
0.8103	Intermediate Similarity	NPC131718
0.8103	Intermediate Similarity	NPC44773
0.8095	Intermediate Similarity	NPC314372
0.8085	Intermediate Similarity	NPC133366
0.8073	Intermediate Similarity	NPC193761
0.8066	Intermediate Similarity	NPC213468
0.8051	Intermediate Similarity	NPC87755
0.8045	Intermediate Similarity	NPC34508
0.8035	Intermediate Similarity	NPC51054
0.8033	Intermediate Similarity	NPC48938
0.8033	Intermediate Similarity	NPC469358
0.8021	Intermediate Similarity	NPC300183
0.8011	Intermediate Similarity	NPC248454
0.8011	Intermediate Similarity	NPC326575
0.8	Intermediate Similarity	NPC315555
0.7989	Intermediate Similarity	NPC129721
0.7978	Intermediate Similarity	NPC71037
0.7976	Intermediate Similarity	NPC190296
0.797	Intermediate Similarity	NPC475422
0.7969	Intermediate Similarity	NPC470497
0.7956	Intermediate Similarity	NPC24594
0.7956	Intermediate Similarity	NPC472122
0.7956	Intermediate Similarity	NPC203754
0.7956	Intermediate Similarity	NPC150048
0.7955	Intermediate Similarity	NPC16667
0.7946	Intermediate Similarity	NPC62510
0.7931	Intermediate Similarity	NPC285469
0.7929	Intermediate Similarity	NPC208284
0.7927	Intermediate Similarity	NPC475506
0.7907	Intermediate Similarity	NPC24678
0.7907	Intermediate Similarity	NPC105818
0.7903	Intermediate Similarity	NPC171171
0.7901	Intermediate Similarity	NPC472586
0.7897	Intermediate Similarity	NPC475070
0.7892	Intermediate Similarity	NPC472294
0.7887	Intermediate Similarity	NPC476874
0.7887	Intermediate Similarity	NPC155143
0.7879	Intermediate Similarity	NPC234999
0.7879	Intermediate Similarity	NPC5145
0.7876	Intermediate Similarity	NPC79129
0.7876	Intermediate Similarity	NPC81654
0.7876	Intermediate Similarity	NPC249150
0.7876	Intermediate Similarity	NPC195461
0.7876	Intermediate Similarity	NPC313985
0.7876	Intermediate Similarity	NPC49196
0.7872	Intermediate Similarity	NPC469501
0.7872	Intermediate Similarity	NPC469470
0.7869	Intermediate Similarity	NPC472443
0.7869	Intermediate Similarity	NPC270009
0.7865	Intermediate Similarity	NPC265576
0.7865	Intermediate Similarity	NPC470508
0.7865	Intermediate Similarity	NPC50503
0.7865	Intermediate Similarity	NPC473640
0.7857	Intermediate Similarity	NPC267885
0.7846	Intermediate Similarity	NPC98715
0.7845	Intermediate Similarity	NPC97525
0.7842	Intermediate Similarity	NPC267343
0.7826	Intermediate Similarity	NPC187827
0.7826	Intermediate Similarity	NPC472105
0.7819	Intermediate Similarity	NPC213629
0.7817	Intermediate Similarity	NPC323927
0.7807	Intermediate Similarity	NPC235684
0.7807	Intermediate Similarity	NPC94752
0.7802	Intermediate Similarity	NPC110500
0.7802	Intermediate Similarity	NPC149155
0.7802	Intermediate Similarity	NPC203468
0.7798	Intermediate Similarity	NPC73767
0.7796	Intermediate Similarity	NPC204717
0.7795	Intermediate Similarity	NPC476073
0.7795	Intermediate Similarity	NPC474116
0.7795	Intermediate Similarity	NPC162730
0.7789	Intermediate Similarity	NPC99666
0.7784	Intermediate Similarity	NPC192270
0.7784	Intermediate Similarity	NPC249040
0.7778	Intermediate Similarity	NPC329858
0.7778	Intermediate Similarity	NPC127677
0.7778	Intermediate Similarity	NPC78020
0.7778	Intermediate Similarity	NPC258062
0.7778	Intermediate Similarity	NPC159856
0.7772	Intermediate Similarity	NPC470499
0.7772	Intermediate Similarity	NPC203614
0.7772	Intermediate Similarity	NPC133261
0.7772	Intermediate Similarity	NPC248041
0.7772	Intermediate Similarity	NPC126709
0.7772	Intermediate Similarity	NPC204491
0.7771	Intermediate Similarity	NPC207726
0.7766	Intermediate Similarity	NPC46580
0.776	Intermediate Similarity	NPC205403
0.776	Intermediate Similarity	NPC11445
0.7754	Intermediate Similarity	NPC314002
0.7754	Intermediate Similarity	NPC476319
0.7751	Intermediate Similarity	NPC469767
0.7751	Intermediate Similarity	NPC469779
0.7751	Intermediate Similarity	NPC469784
0.7751	Intermediate Similarity	NPC469761
0.7751	Intermediate Similarity	NPC469783
0.7751	Intermediate Similarity	NPC469780
0.7751	Intermediate Similarity	NPC469768
0.7742	Intermediate Similarity	NPC472444
0.7742	Intermediate Similarity	NPC220765
0.774	Intermediate Similarity	NPC92796
0.774	Intermediate Similarity	NPC135141
0.774	Intermediate Similarity	NPC67056
0.7739	Intermediate Similarity	NPC271862
0.7732	Intermediate Similarity	NPC100321
0.7732	Intermediate Similarity	NPC32200
0.773	Intermediate Similarity	NPC15840
0.7727	Intermediate Similarity	NPC166492
0.7727	Intermediate Similarity	NPC225821
0.7727	Intermediate Similarity	NPC46225
0.7727	Intermediate Similarity	NPC473362
0.7725	Intermediate Similarity	NPC175474
0.7725	Intermediate Similarity	NPC321708
0.772	Intermediate Similarity	NPC227582
0.7717	Intermediate Similarity	NPC14113
0.7717	Intermediate Similarity	NPC145885
0.7717	Intermediate Similarity	NPC111275
0.7717	Intermediate Similarity	NPC84827
0.7716	Intermediate Similarity	NPC470505
0.7716	Intermediate Similarity	NPC470500
0.7711	Intermediate Similarity	NPC87856
0.7711	Intermediate Similarity	NPC151976
0.7711	Intermediate Similarity	NPC475778
0.7709	Intermediate Similarity	NPC78375
0.7709	Intermediate Similarity	NPC469813
0.7709	Intermediate Similarity	NPC476446
0.7708	Intermediate Similarity	NPC157828
0.7708	Intermediate Similarity	NPC195239

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 NPC95783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	535
0.2-0.3	843
0.3-0.4	1507
0.4-0.5	2717
0.5-0.6	2093
0.6-0.7	984
0.7-0.8	213
0.8-0.85	25
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9012	High Similarity	NPD4076	Approved
0.9012	High Similarity	NPD4079	Approved
0.8953	High Similarity	NPD3505	Approved
0.8953	High Similarity	NPD3506	Approved
0.8895	High Similarity	NPD6375	Clinical (unspecified phase)
0.8547	High Similarity	NPD6610	Clinical (unspecified phase)
0.8538	High Similarity	NPD3323	Discontinued
0.8523	High Similarity	NPD4181	Approved
0.8514	High Similarity	NPD5065	Approved
0.8497	Intermediate Similarity	NPD4640	Approved
0.8497	Intermediate Similarity	NPD4638	Approved
0.8497	Intermediate Similarity	NPD4639	Approved
0.84	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.836	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD8431	Approved
0.8343	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD6595	Phase 3
0.8315	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD3610	Approved
0.8295	Intermediate Similarity	NPD3609	Approved
0.829	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.8251	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1325	Approved
0.8239	Intermediate Similarity	NPD1326	Approved
0.8202	Intermediate Similarity	NPD4128	Approved
0.8162	Intermediate Similarity	NPD6281	Approved
0.8156	Intermediate Similarity	NPD4075	Phase 2
0.8111	Intermediate Similarity	NPD2144	Approved
0.8105	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD3038	Discontinued
0.8045	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD3404	Approved
0.7978	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD3961	Discontinued
0.7937	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1722	Approved
0.7906	Intermediate Similarity	NPD6664	Approved
0.7902	Intermediate Similarity	NPD7271	Approved
0.7897	Intermediate Similarity	NPD5426	Phase 3
0.7895	Intermediate Similarity	NPD4702	Approved
0.7895	Intermediate Similarity	NPD4703	Approved
0.7877	Intermediate Similarity	NPD5021	Discontinued
0.7876	Intermediate Similarity	NPD4601	Approved
0.7876	Intermediate Similarity	NPD4600	Approved
0.7857	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5100	Phase 3
0.7857	Intermediate Similarity	NPD7957	Phase 1
0.7849	Intermediate Similarity	NPD3100	Discontinued
0.7826	Intermediate Similarity	NPD7731	Approved
0.7826	Intermediate Similarity	NPD7730	Approved
0.7812	Intermediate Similarity	NPD7948	Phase 1
0.7802	Intermediate Similarity	NPD482	Approved
0.7798	Intermediate Similarity	NPD786	Approved
0.7796	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD5315	Discontinued
0.7751	Intermediate Similarity	NPD7824	Approved
0.7742	Intermediate Similarity	NPD2094	Phase 2
0.7742	Intermediate Similarity	NPD2092	Phase 2
0.7742	Intermediate Similarity	NPD2095	Phase 2
0.7727	Intermediate Similarity	NPD6026	Approved
0.7727	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5254	Discontinued
0.7716	Intermediate Similarity	NPD5901	Discontinued
0.7701	Intermediate Similarity	NPD2096	Phase 2
0.7701	Intermediate Similarity	NPD2091	Phase 2
0.768	Intermediate Similarity	NPD2641	Approved
0.768	Intermediate Similarity	NPD2640	Approved
0.7665	Intermediate Similarity	NPD8072	Approved
0.7663	Intermediate Similarity	NPD2381	Approved
0.7663	Intermediate Similarity	NPD2380	Approved
0.7663	Intermediate Similarity	NPD2382	Approved
0.765	Intermediate Similarity	NPD750	Phase 2
0.7644	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7953	Approved
0.7642	Intermediate Similarity	NPD7951	Approved
0.7642	Intermediate Similarity	NPD7952	Approved
0.7642	Intermediate Similarity	NPD7950	Approved
0.7642	Intermediate Similarity	NPD7789	Approved
0.7642	Intermediate Similarity	NPD7790	Approved
0.7642	Intermediate Similarity	NPD7791	Approved
0.7635	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD8272	Phase 2
0.7619	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD2837	Discontinued
0.76	Intermediate Similarity	NPD2172	Phase 1
0.7592	Intermediate Similarity	NPD4499	Approved
0.7588	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8094	Discontinued
0.7582	Intermediate Similarity	NPD5862	Discovery
0.7581	Intermediate Similarity	NPD8386	Phase 2
0.7579	Intermediate Similarity	NPD8020	Approved
0.7579	Intermediate Similarity	NPD8021	Approved
0.7574	Intermediate Similarity	NPD7470	Discontinued
0.7566	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD1038	Approved
0.7565	Intermediate Similarity	NPD802	Phase 2
0.7563	Intermediate Similarity	NPD4511	Phase 1
0.7558	Intermediate Similarity	NPD3717	Discontinued
0.7552	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD5913	Phase 3
0.7551	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7233	Approved
0.7539	Intermediate Similarity	NPD7234	Approved
0.7537	Intermediate Similarity	NPD8093	Discontinued
0.7529	Intermediate Similarity	NPD1683	Approved
0.7526	Intermediate Similarity	NPD7944	Discontinued
0.7526	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD8073	Approved
0.75	Intermediate Similarity	NPD4463	Approved
0.75	Intermediate Similarity	NPD4462	Approved
0.7487	Intermediate Similarity	NPD2383	Phase 1
0.7487	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD5596	Phase 2
0.7459	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2882	Phase 1
0.7457	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7780	Approved
0.7453	Intermediate Similarity	NPD7781	Approved
0.7451	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3330	Phase 1
0.7447	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5255	Approved
0.7442	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD8123	Approved
0.7433	Intermediate Similarity	NPD8122	Approved
0.7429	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD2510	Approved
0.7426	Intermediate Similarity	NPD2509	Approved
0.7414	Intermediate Similarity	NPD3813	Approved
0.7406	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD6978	Phase 2
0.7403	Intermediate Similarity	NPD1403	Approved
0.7403	Intermediate Similarity	NPD1404	Approved
0.7402	Intermediate Similarity	NPD5939	Approved
0.7402	Intermediate Similarity	NPD5936	Approved
0.7393	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4547	Phase 3
0.7377	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1392	Approved
0.7374	Intermediate Similarity	NPD2176	Approved
0.7374	Intermediate Similarity	NPD2175	Phase 3
0.7374	Intermediate Similarity	NPD2177	Approved
0.736	Intermediate Similarity	NPD6158	Phase 2
0.736	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3013	Phase 3
0.7353	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7619	Phase 3
0.7347	Intermediate Similarity	NPD7618	Phase 3
0.7343	Intermediate Similarity	NPD3393	Approved
0.7343	Intermediate Similarity	NPD3394	Approved
0.7343	Intermediate Similarity	NPD3389	Approved
0.7337	Intermediate Similarity	NPD6479	Discontinued
0.7337	Intermediate Similarity	NPD2639	Approved
0.7337	Intermediate Similarity	NPD2642	Approved
0.7333	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2928	Phase 2
0.7322	Intermediate Similarity	NPD3583	Phase 2
0.732	Intermediate Similarity	NPD8063	Discontinued
0.732	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5066	Phase 2
0.7317	Intermediate Similarity	NPD5067	Phase 2
0.7316	Intermediate Similarity	NPD8408	Discontinued
0.7315	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4886	Phase 2
0.7312	Intermediate Similarity	NPD3117	Approved
0.7312	Intermediate Similarity	NPD3116	Approved
0.7308	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6995	Phase 1
0.7292	Intermediate Similarity	NPD3082	Discontinued
0.7286	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6999	Discontinued
0.7282	Intermediate Similarity	NPD4699	Discontinued
0.7277	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4795	Phase 2
0.7268	Intermediate Similarity	NPD8026	Phase 1
0.7264	Intermediate Similarity	NPD6975	Discontinued
0.726	Intermediate Similarity	NPD5612	Discontinued
0.7255	Intermediate Similarity	NPD2916	Discontinued
0.7254	Intermediate Similarity	NPD6217	Discontinued

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