NPASS Compound

Structure

NPC286135 OpenBabel07101719122D 27 30 0 0 1 0 0 0 0 0999 V2000 -1.6168 -2.4557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7361 -4.2544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4126 -1.2818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8164 0.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7626 -3.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -3.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 -2.3523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0962 -2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7653 -1.8171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4563 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -1.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9706 -0.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6386 -2.6637 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -0.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4052 -3.5113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7435 -2.0250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1254 -0.1229 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 20 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 20 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 11 17 1 0 0 0 0 11 21 1 1 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 19 1 6 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 10 1 6 0 0 0 19 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	377.15
Volume:	362.3
LogP:	0.701
LogD:	0.734
LogS:	-2.499
# Rotatable Bonds:	3
TPSA:	97.69
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	4.832
Fsp3:	0.526
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:	-4.95
MDCK Permeability:	3.582646604627371e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.66
Human Intestinal Absorption (HIA):	0.181
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.721

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	35.34439468383789%
Volume Distribution (VD):	1.697
Pgp-substrate:	44.89098358154297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.819
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.234
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.475
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.73

ADMET: Excretion

Clearance (CL):	6.352
Half-life (T1/2):	0.649

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.757
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.424
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.039
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC286135

Natural Product ID:	NPC286135
*Common Name:**	10-O-Methylhostasine
IUPAC Name:	(3R,5'S,6'R,7'aR)-5',6'-dihydroxy-5,6,7-trimethoxy-1'-methylspiro[2-benzofuran-3,7'-3,5,6,7a-tetrahydro-2H-indole]-1-one
Synonyms:	10-O-Methylhostasine
Standard InCHIKey:	ARKFTBZTMGGQCK-GIYVSIDVSA-N
Standard InCHI:	InChI=1S/C19H23NO7/c1-20-6-5-9-7-11(21)17(22)19(16(9)20)10-8-12(24-2)14(25-3)15(26-4)13(10)18(23)27-19/h7-8,11,16-17,21-22H,5-6H2,1-4H3/t11-,16+,17+,19+/m0/s1
SMILES:	COc1cc2c(c(c1OC)OC)C(=O)O[C@@]12[C@H](O)[C@@H](O)C=C2[C@H]1N(C)CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL250688
PubChem CID:	23642826
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004122] Homolycorine-type amaryllidaceae alkaloids

*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
NPO22974	Hosta plantaginea	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822295]
NPO22974	Hosta plantaginea	Species	Asparagaceae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	113000.0	nM	PMID[488087]

☑ 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 NPC286135 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	282
0.1-0.2	1254
0.2-0.3	3952
0.3-0.4	10044
0.4-0.5	8133
0.5-0.6	7161
0.6-0.7	10296
0.7-0.8	1523
0.8-0.85	40
0.85-0.9	9
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC94499
0.9409	High Similarity	NPC80472
0.8824	High Similarity	NPC33256
0.8703	High Similarity	NPC162694
0.8646	High Similarity	NPC328700
0.8646	High Similarity	NPC202771
0.8646	High Similarity	NPC2173
0.8646	High Similarity	NPC119818
0.8525	High Similarity	NPC35680
0.8438	Intermediate Similarity	NPC46744
0.8438	Intermediate Similarity	NPC73020
0.8438	Intermediate Similarity	NPC14622
0.8438	Intermediate Similarity	NPC70290
0.8438	Intermediate Similarity	NPC124302
0.8438	Intermediate Similarity	NPC215098
0.836	Intermediate Similarity	NPC141440
0.8351	Intermediate Similarity	NPC120671
0.8351	Intermediate Similarity	NPC226652
0.8351	Intermediate Similarity	NPC72788
0.8351	Intermediate Similarity	NPC314100
0.8196	Intermediate Similarity	NPC204580
0.8191	Intermediate Similarity	NPC473562
0.8177	Intermediate Similarity	NPC226708
0.8158	Intermediate Similarity	NPC18306
0.8154	Intermediate Similarity	NPC83019
0.8105	Intermediate Similarity	NPC474746
0.8105	Intermediate Similarity	NPC475981
0.8022	Intermediate Similarity	NPC26353
0.8022	Intermediate Similarity	NPC77679
0.8022	Intermediate Similarity	NPC190020
0.8022	Intermediate Similarity	NPC84935
0.8021	Intermediate Similarity	NPC230098
0.801	Intermediate Similarity	NPC475566
0.7989	Intermediate Similarity	NPC329816
0.798	Intermediate Similarity	NPC476661
0.7967	Intermediate Similarity	NPC150227
0.7947	Intermediate Similarity	NPC474745
0.794	Intermediate Similarity	NPC476662
0.7926	Intermediate Similarity	NPC329992
0.7912	Intermediate Similarity	NPC199926
0.7912	Intermediate Similarity	NPC79998
0.7912	Intermediate Similarity	NPC16082
0.7912	Intermediate Similarity	NPC82592
0.7897	Intermediate Similarity	NPC63152
0.7895	Intermediate Similarity	NPC474325
0.7895	Intermediate Similarity	NPC309692
0.7892	Intermediate Similarity	NPC35345
0.7887	Intermediate Similarity	NPC166979
0.7887	Intermediate Similarity	NPC315914
0.7868	Intermediate Similarity	NPC125924
0.7857	Intermediate Similarity	NPC281477
0.785	Intermediate Similarity	NPC201055
0.785	Intermediate Similarity	NPC254045
0.785	Intermediate Similarity	NPC151470
0.785	Intermediate Similarity	NPC64576
0.7843	Intermediate Similarity	NPC46990
0.7842	Intermediate Similarity	NPC237044
0.7828	Intermediate Similarity	NPC66909
0.7817	Intermediate Similarity	NPC469815
0.7817	Intermediate Similarity	NPC469816
0.7806	Intermediate Similarity	NPC319549
0.7806	Intermediate Similarity	NPC196231
0.7796	Intermediate Similarity	NPC117985
0.7795	Intermediate Similarity	NPC208890
0.779	Intermediate Similarity	NPC179178
0.779	Intermediate Similarity	NPC96501
0.7789	Intermediate Similarity	NPC304675
0.7778	Intermediate Similarity	NPC129578
0.776	Intermediate Similarity	NPC244554
0.7754	Intermediate Similarity	NPC474858
0.7747	Intermediate Similarity	NPC240768
0.7747	Intermediate Similarity	NPC200773
0.7731	Intermediate Similarity	NPC211215
0.7725	Intermediate Similarity	NPC20237
0.7713	Intermediate Similarity	NPC249181
0.7701	Intermediate Similarity	NPC180306
0.7696	Intermediate Similarity	NPC476500
0.7696	Intermediate Similarity	NPC314946
0.7688	Intermediate Similarity	NPC470339
0.7684	Intermediate Similarity	NPC283041
0.7672	Intermediate Similarity	NPC191930
0.7668	Intermediate Similarity	NPC99179
0.7661	Intermediate Similarity	NPC316292
0.7656	Intermediate Similarity	NPC474470
0.7654	Intermediate Similarity	NPC27106
0.765	Intermediate Similarity	NPC473732
0.765	Intermediate Similarity	NPC215921
0.765	Intermediate Similarity	NPC70016
0.7647	Intermediate Similarity	NPC472055
0.7637	Intermediate Similarity	NPC237440
0.7637	Intermediate Similarity	NPC270160
0.7635	Intermediate Similarity	NPC67346
0.7634	Intermediate Similarity	NPC4304
0.7632	Intermediate Similarity	NPC474708
0.7624	Intermediate Similarity	NPC474427
0.7619	Intermediate Similarity	NPC252960
0.7614	Intermediate Similarity	NPC469437
0.761	Intermediate Similarity	NPC475768
0.7609	Intermediate Similarity	NPC475116
0.7602	Intermediate Similarity	NPC9867
0.7592	Intermediate Similarity	NPC471180
0.7581	Intermediate Similarity	NPC227062
0.7581	Intermediate Similarity	NPC472050
0.758	Intermediate Similarity	NPC185031
0.7579	Intermediate Similarity	NPC475845
0.7577	Intermediate Similarity	NPC27887
0.7574	Intermediate Similarity	NPC207239
0.7566	Intermediate Similarity	NPC329717
0.7565	Intermediate Similarity	NPC471181
0.7562	Intermediate Similarity	NPC474432
0.7562	Intermediate Similarity	NPC24228
0.7562	Intermediate Similarity	NPC475713
0.7554	Intermediate Similarity	NPC228662
0.7553	Intermediate Similarity	NPC200594
0.7553	Intermediate Similarity	NPC474770
0.7553	Intermediate Similarity	NPC218614
0.7549	Intermediate Similarity	NPC97086
0.7549	Intermediate Similarity	NPC140577
0.7549	Intermediate Similarity	NPC43069
0.754	Intermediate Similarity	NPC473395
0.754	Intermediate Similarity	NPC246466
0.7539	Intermediate Similarity	NPC472452
0.7539	Intermediate Similarity	NPC119589
0.7539	Intermediate Similarity	NPC170245
0.7538	Intermediate Similarity	NPC477816
0.7526	Intermediate Similarity	NPC190332
0.7526	Intermediate Similarity	NPC181653
0.7526	Intermediate Similarity	NPC57812
0.7526	Intermediate Similarity	NPC475985
0.7526	Intermediate Similarity	NPC474324
0.7525	Intermediate Similarity	NPC293624
0.7524	Intermediate Similarity	NPC315253
0.7523	Intermediate Similarity	NPC44040
0.7514	Intermediate Similarity	NPC167903
0.7513	Intermediate Similarity	NPC349525
0.7513	Intermediate Similarity	NPC17219
0.7512	Intermediate Similarity	NPC470646
0.75	Intermediate Similarity	NPC180210
0.75	Intermediate Similarity	NPC469619
0.75	Intermediate Similarity	NPC470739
0.75	Intermediate Similarity	NPC469670
0.75	Intermediate Similarity	NPC477410
0.75	Intermediate Similarity	NPC321226
0.75	Intermediate Similarity	NPC473094
0.75	Intermediate Similarity	NPC477640
0.75	Intermediate Similarity	NPC227683
0.75	Intermediate Similarity	NPC51106
0.75	Intermediate Similarity	NPC328856
0.75	Intermediate Similarity	NPC314914
0.75	Intermediate Similarity	NPC478046
0.75	Intermediate Similarity	NPC316164
0.75	Intermediate Similarity	NPC225597
0.75	Intermediate Similarity	NPC478047
0.7487	Intermediate Similarity	NPC300053
0.7487	Intermediate Similarity	NPC326520
0.7487	Intermediate Similarity	NPC54928
0.7476	Intermediate Similarity	NPC169605
0.7474	Intermediate Similarity	NPC476002
0.7473	Intermediate Similarity	NPC32058
0.7473	Intermediate Similarity	NPC85734
0.7473	Intermediate Similarity	NPC260946
0.7473	Intermediate Similarity	NPC470357
0.7473	Intermediate Similarity	NPC192189
0.7473	Intermediate Similarity	NPC43872
0.7473	Intermediate Similarity	NPC238672
0.7473	Intermediate Similarity	NPC197188
0.7473	Intermediate Similarity	NPC116850
0.7473	Intermediate Similarity	NPC144801
0.7473	Intermediate Similarity	NPC291510
0.7465	Intermediate Similarity	NPC316368
0.7465	Intermediate Similarity	NPC82056
0.7465	Intermediate Similarity	NPC284236
0.7463	Intermediate Similarity	NPC232533
0.7463	Intermediate Similarity	NPC243483
0.7461	Intermediate Similarity	NPC473095
0.7461	Intermediate Similarity	NPC473096
0.746	Intermediate Similarity	NPC155302
0.746	Intermediate Similarity	NPC161947
0.746	Intermediate Similarity	NPC24627
0.7459	Intermediate Similarity	NPC210425
0.7459	Intermediate Similarity	NPC277426
0.7459	Intermediate Similarity	NPC280404
0.7459	Intermediate Similarity	NPC86373
0.7453	Intermediate Similarity	NPC478048
0.7453	Intermediate Similarity	NPC38964
0.7449	Intermediate Similarity	NPC324220
0.7449	Intermediate Similarity	NPC312630
0.7448	Intermediate Similarity	NPC474475
0.7448	Intermediate Similarity	NPC165460
0.7448	Intermediate Similarity	NPC75958
0.7447	Intermediate Similarity	NPC249274
0.7447	Intermediate Similarity	NPC205167
0.7444	Intermediate Similarity	NPC469579
0.7436	Intermediate Similarity	NPC327005
0.7435	Intermediate Similarity	NPC124038
0.7435	Intermediate Similarity	NPC100566
0.7435	Intermediate Similarity	NPC476822
0.7433	Intermediate Similarity	NPC16286
0.7432	Intermediate Similarity	NPC166583
0.7432	Intermediate Similarity	NPC53362

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 NPC286135 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	567
0.2-0.3	1400
0.3-0.4	2337
0.4-0.5	2416
0.5-0.6	1479
0.6-0.7	662
0.7-0.8	94
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8646	High Similarity	NPD5006	Approved
0.8646	High Similarity	NPD5005	Approved
0.8438	Intermediate Similarity	NPD4420	Approved
0.7947	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD5710	Approved
0.7946	Intermediate Similarity	NPD5711	Approved
0.7943	Intermediate Similarity	NPD7907	Approved
0.7933	Intermediate Similarity	NPD4111	Phase 1
0.7933	Intermediate Similarity	NPD4665	Approved
0.785	Intermediate Similarity	NPD2494	Approved
0.785	Intermediate Similarity	NPD3452	Approved
0.785	Intermediate Similarity	NPD3450	Approved
0.785	Intermediate Similarity	NPD2493	Approved
0.7828	Intermediate Similarity	NPD2975	Approved
0.7828	Intermediate Similarity	NPD2973	Approved
0.7828	Intermediate Similarity	NPD2974	Approved
0.7807	Intermediate Similarity	NPD5242	Approved
0.7806	Intermediate Similarity	NPD7296	Approved
0.78	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD4583	Approved
0.7734	Intermediate Similarity	NPD4582	Approved
0.7717	Intermediate Similarity	NPD5353	Approved
0.7711	Intermediate Similarity	NPD4580	Approved
0.7685	Intermediate Similarity	NPD4004	Approved
0.7685	Intermediate Similarity	NPD4002	Approved
0.7636	Intermediate Similarity	NPD7048	Phase 3
0.7635	Intermediate Similarity	NPD3057	Approved
0.7617	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD5676	Approved
0.759	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6625	Approved
0.7574	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6386	Approved
0.7554	Intermediate Similarity	NPD6385	Approved
0.7549	Intermediate Similarity	NPD3533	Approved
0.7549	Intermediate Similarity	NPD2972	Approved
0.7537	Intermediate Similarity	NPD4107	Approved
0.7512	Intermediate Similarity	NPD4361	Phase 2
0.7512	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7930	Approved
0.7488	Intermediate Similarity	NPD6997	Phase 2
0.7463	Intermediate Similarity	NPD3448	Approved
0.7463	Intermediate Similarity	NPD2491	Approved
0.7453	Intermediate Similarity	NPD7047	Phase 3
0.7415	Intermediate Similarity	NPD4482	Phase 3
0.74	Intermediate Similarity	NPD2488	Approved
0.74	Intermediate Similarity	NPD2490	Approved
0.7393	Intermediate Similarity	NPD7827	Phase 1
0.7368	Intermediate Similarity	NPD7701	Phase 2
0.7343	Intermediate Similarity	NPD7497	Discontinued
0.7322	Intermediate Similarity	NPD2533	Approved
0.7322	Intermediate Similarity	NPD2532	Approved
0.7322	Intermediate Similarity	NPD2534	Approved
0.7317	Intermediate Similarity	NPD7565	Approved
0.7313	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7906	Approved
0.7292	Intermediate Similarity	NPD6232	Discontinued
0.7291	Intermediate Similarity	NPD3473	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2968	Approved
0.7273	Intermediate Similarity	NPD2971	Approved
0.7273	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7039	Approved
0.7259	Intermediate Similarity	NPD7038	Approved
0.7256	Intermediate Similarity	NPD8404	Phase 2
0.7255	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2969	Approved
0.7254	Intermediate Similarity	NPD2970	Approved
0.725	Intermediate Similarity	NPD4663	Approved
0.7238	Intermediate Similarity	NPD2654	Approved
0.7238	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8319	Approved
0.7225	Intermediate Similarity	NPD8320	Phase 1
0.7216	Intermediate Similarity	NPD4481	Phase 3
0.7211	Intermediate Similarity	NPD4967	Phase 2
0.7211	Intermediate Similarity	NPD4966	Approved
0.7211	Intermediate Similarity	NPD4965	Approved
0.7206	Intermediate Similarity	NPD4363	Phase 3
0.7206	Intermediate Similarity	NPD4360	Phase 2
0.7202	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5036	Approved
0.7194	Intermediate Similarity	NPD5312	Approved
0.7194	Intermediate Similarity	NPD5313	Approved
0.719	Intermediate Similarity	NPD7999	Approved
0.7189	Intermediate Similarity	NPD2899	Discontinued
0.7186	Intermediate Similarity	NPD4578	Approved
0.7186	Intermediate Similarity	NPD4577	Approved
0.7183	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7783	Phase 2
0.7179	Intermediate Similarity	NPD7473	Discontinued
0.7164	Intermediate Similarity	NPD5037	Approved
0.7164	Intermediate Similarity	NPD5038	Approved
0.7158	Intermediate Similarity	NPD2560	Approved
0.7158	Intermediate Similarity	NPD2563	Approved
0.715	Intermediate Similarity	NPD8285	Discontinued
0.7143	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4237	Approved
0.7143	Intermediate Similarity	NPD1934	Approved
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD4236	Phase 3
0.7135	Intermediate Similarity	NPD6234	Discontinued
0.7128	Intermediate Similarity	NPD2489	Approved
0.7128	Intermediate Similarity	NPD27	Approved
0.712	Intermediate Similarity	NPD3882	Suspended
0.7113	Intermediate Similarity	NPD3051	Approved
0.7112	Intermediate Similarity	NPD4210	Discontinued
0.7107	Intermediate Similarity	NPD5844	Phase 1
0.7105	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7311	Approved
0.71	Intermediate Similarity	NPD7312	Approved
0.71	Intermediate Similarity	NPD7313	Approved
0.71	Intermediate Similarity	NPD7310	Approved
0.7089	Intermediate Similarity	NPD8151	Discontinued
0.7088	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3817	Phase 2
0.7065	Intermediate Similarity	NPD7309	Approved
0.7053	Intermediate Similarity	NPD37	Approved
0.7033	Intermediate Similarity	NPD6781	Approved
0.7033	Intermediate Similarity	NPD6780	Approved
0.7033	Intermediate Similarity	NPD6776	Approved
0.7033	Intermediate Similarity	NPD6777	Approved
0.7033	Intermediate Similarity	NPD6779	Approved
0.7033	Intermediate Similarity	NPD6778	Approved
0.7033	Intermediate Similarity	NPD6782	Approved
0.7031	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4846	Phase 2
0.7018	Intermediate Similarity	NPD5980	Discovery
0.7016	Intermediate Similarity	NPD2801	Approved
0.701	Intermediate Similarity	NPD5494	Approved
0.701	Intermediate Similarity	NPD6836	Approved
0.7	Intermediate Similarity	NPD5030	Phase 2
0.6995	Remote Similarity	NPD7583	Approved
0.6981	Remote Similarity	NPD4040	Phase 1
0.6977	Remote Similarity	NPD7874	Approved
0.6977	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6107	Approved
0.697	Remote Similarity	NPD7228	Approved
0.697	Remote Similarity	NPD2163	Approved
0.6965	Remote Similarity	NPD5026	Approved
0.6965	Remote Similarity	NPD36	Approved
0.6965	Remote Similarity	NPD7549	Discontinued
0.6965	Remote Similarity	NPD4955	Approved
0.6965	Remote Similarity	NPD5034	Approved
0.6965	Remote Similarity	NPD4954	Approved
0.6965	Remote Similarity	NPD5028	Approved
0.6964	Remote Similarity	NPD8469	Approved
0.6963	Remote Similarity	NPD7585	Approved
0.6954	Remote Similarity	NPD6166	Phase 2
0.6954	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6071	Discontinued
0.6939	Remote Similarity	NPD7315	Approved
0.6934	Remote Similarity	NPD7697	Approved
0.6934	Remote Similarity	NPD7698	Approved
0.6934	Remote Similarity	NPD7696	Phase 3
0.6931	Remote Similarity	NPD3686	Approved
0.6931	Remote Similarity	NPD7281	Phase 3
0.6931	Remote Similarity	NPD3687	Approved
0.6931	Remote Similarity	NPD7280	Phase 3
0.6927	Remote Similarity	NPD5772	Approved
0.6927	Remote Similarity	NPD5773	Approved
0.6927	Remote Similarity	NPD7819	Suspended
0.6916	Remote Similarity	NPD7584	Approved
0.6915	Remote Similarity	NPD5029	Approved
0.6915	Remote Similarity	NPD5027	Approved
0.6915	Remote Similarity	NPD5031	Approved
0.6912	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7870	Phase 2
0.6901	Remote Similarity	NPD7871	Phase 2
0.69	Remote Similarity	NPD7074	Phase 3
0.6897	Remote Similarity	NPD8054	Approved
0.6897	Remote Similarity	NPD8053	Approved
0.6897	Remote Similarity	NPD6853	Approved
0.6897	Remote Similarity	NPD6851	Approved
0.6895	Remote Similarity	NPD824	Approved
0.6895	Remote Similarity	NPD3455	Phase 2
0.6889	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8059	Phase 3
0.6888	Remote Similarity	NPD7199	Phase 2
0.6884	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7177	Discontinued
0.6882	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5241	Discontinued
0.6881	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD2898	Approved
0.6869	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3823	Discontinued
0.6864	Remote Similarity	NPD8152	Approved
0.6864	Remote Similarity	NPD8153	Approved
0.6859	Remote Similarity	NPD4380	Phase 2
0.685	Remote Similarity	NPD7054	Approved
0.6845	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD8491	Approved
0.6839	Remote Similarity	NPD1465	Phase 2
0.6839	Remote Similarity	NPD2977	Approved
0.6839	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2978	Approved
0.6839	Remote Similarity	NPD4585	Approved
0.6837	Remote Similarity	NPD4666	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data