NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	327.15
Volume:	333.293
LogP:	1.789
LogD:	2.38
LogS:	-1.545
# Rotatable Bonds:	3
TPSA:	59.95
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.908
Synthetic Accessibility Score:	3.139
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.129
MDCK Permeability:	1.4011184248374775e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.961
Plasma Protein Binding (PPB):	83.04254913330078%
Volume Distribution (VD):	1.714
Pgp-substrate:	15.794740676879883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.234
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.674
CYP2D6-inhibitor:	0.118
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	4.958
Half-life (T1/2):	0.377

ADMET: Toxicity

hERG Blockers:	0.504
Human Hepatotoxicity (H-HT):	0.367
Drug-inuced Liver Injury (DILI):	0.413
AMES Toxicity:	0.43
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.501
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC477020

Natural Product ID:	NPC477020
*Common Name:**	(6aS)-1,2,10-trimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol;2,2,2-trifluoroacetic acid
IUPAC Name:	(6aS)-1,2,10-trimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol;2,2,2-trifluoroacetic acid
Synonyms:	(S)-Isocorydine
Standard InCHIKey:	SZTOTPMSXDBOID-YDALLXLXSA-N
Standard InCHI:	InChI=1S/C19H21NO4.C2HF3O2/c1-22-13-5-4-10-8-12-15-11(6-7-20-12)9-14(23-2)19(24-3)17(15)16(10)18(13)21;3-2(4,5)1(6)7/h4-5,9,12,20-21H,6-8H2,1-3H3;(H,6,7)/t12-;/m0./s1
SMILES:	COC1=C(C2=C(C[C@H]3C4=C2C(=C(C=C4CCN3)OC)OC)C=C1)O.C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49797713
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO23314	Doryphora sassafras	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754616]
NPO23314	Doryphora sassafras	Species	Atherospermataceae	Eukaryota	leaves	The Head, 1.5 km NW of Wilsons Peak, Darling Downs, Queensland, Australia	1994-AUG	PMID[19637893]
NPO23314	Doryphora sassafras	Species	Atherospermataceae	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	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	0	%	PMID[19637893]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	19000	nM	PMID[19637893]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	17000	nM	PMID[19637893]

☑ 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 NPC477020 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	262
0.1-0.2	1382
0.2-0.3	6503
0.3-0.4	11607
0.4-0.5	5480
0.5-0.6	12251
0.6-0.7	4385
0.7-0.8	611
0.8-0.85	139
0.85-0.9	46
0.9-0.95	26
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC66341
1.0	High Similarity	NPC192135
0.9873	High Similarity	NPC26240
0.9873	High Similarity	NPC69712
0.9873	High Similarity	NPC477562
0.9684	High Similarity	NPC35627
0.9684	High Similarity	NPC476573
0.9684	High Similarity	NPC81247
0.9632	High Similarity	NPC474507
0.9623	High Similarity	NPC205421
0.9623	High Similarity	NPC474931
0.9623	High Similarity	NPC81218
0.9623	High Similarity	NPC145832
0.9623	High Similarity	NPC12053
0.9623	High Similarity	NPC306555
0.9623	High Similarity	NPC158376
0.9623	High Similarity	NPC117188
0.9576	High Similarity	NPC135772
0.9509	High Similarity	NPC173416
0.9509	High Similarity	NPC148709
0.9509	High Similarity	NPC476577
0.9497	High Similarity	NPC306843
0.9497	High Similarity	NPC78222
0.9497	High Similarity	NPC212794
0.9497	High Similarity	NPC96603
0.9497	High Similarity	NPC477563
0.9497	High Similarity	NPC13504
0.9497	High Similarity	NPC136508
0.9497	High Similarity	NPC253043
0.9497	High Similarity	NPC196447
0.9455	High Similarity	NPC312918
0.9455	High Similarity	NPC476574
0.9455	High Similarity	NPC155442
0.9455	High Similarity	NPC477561
0.9434	High Similarity	NPC324144
0.9434	High Similarity	NPC1229
0.9308	High Similarity	NPC166014
0.9308	High Similarity	NPC27410
0.9241	High Similarity	NPC126519
0.9241	High Similarity	NPC170503
0.9241	High Similarity	NPC203784
0.9217	High Similarity	NPC114364
0.9217	High Similarity	NPC320223
0.9212	High Similarity	NPC477558
0.9207	High Similarity	NPC239775
0.9182	High Similarity	NPC476572
0.9176	High Similarity	NPC186546
0.9176	High Similarity	NPC476576
0.9146	High Similarity	NPC168753
0.9146	High Similarity	NPC118274
0.9141	High Similarity	NPC204947
0.9118	High Similarity	NPC57036
0.9096	High Similarity	NPC229166
0.9096	High Similarity	NPC199465
0.9096	High Similarity	NPC128560
0.9057	High Similarity	NPC325871
0.9057	High Similarity	NPC99659
0.903	High Similarity	NPC152212
0.903	High Similarity	NPC6152
0.9012	High Similarity	NPC60186
0.8994	High Similarity	NPC2295
0.8994	High Similarity	NPC477564
0.8987	High Similarity	NPC76213
0.8987	High Similarity	NPC277669
0.8982	High Similarity	NPC329969
0.896	High Similarity	NPC475754
0.8882	High Similarity	NPC474506
0.8882	High Similarity	NPC32413
0.8868	High Similarity	NPC326316
0.8868	High Similarity	NPC81733
0.8861	High Similarity	NPC207824
0.8861	High Similarity	NPC60538
0.8848	High Similarity	NPC86144
0.8848	High Similarity	NPC304659
0.883	High Similarity	NPC476575
0.883	High Similarity	NPC116284
0.8824	High Similarity	NPC470879
0.8824	High Similarity	NPC258695
0.8795	High Similarity	NPC298979
0.8795	High Similarity	NPC247389
0.8765	High Similarity	NPC23219
0.8735	High Similarity	NPC24264
0.8735	High Similarity	NPC193853
0.8735	High Similarity	NPC223077
0.8735	High Similarity	NPC476432
0.8735	High Similarity	NPC219341
0.8735	High Similarity	NPC56887
0.8735	High Similarity	NPC195392
0.8727	High Similarity	NPC189470
0.8721	High Similarity	NPC248642
0.8713	High Similarity	NPC267408
0.8706	High Similarity	NPC112575
0.8704	High Similarity	NPC276588
0.8704	High Similarity	NPC2413
0.8704	High Similarity	NPC54379
0.8704	High Similarity	NPC39701
0.8704	High Similarity	NPC204828
0.8704	High Similarity	NPC295691
0.8704	High Similarity	NPC127674
0.8704	High Similarity	NPC189266
0.8704	High Similarity	NPC469817
0.8704	High Similarity	NPC249797
0.8704	High Similarity	NPC207757
0.8704	High Similarity	NPC278799
0.8704	High Similarity	NPC193949
0.8704	High Similarity	NPC184026
0.8704	High Similarity	NPC172765
0.8704	High Similarity	NPC5238
0.8704	High Similarity	NPC110416
0.8693	High Similarity	NPC117717
0.869	High Similarity	NPC109925
0.8679	High Similarity	NPC135538
0.8679	High Similarity	NPC24233
0.8679	High Similarity	NPC147390
0.8679	High Similarity	NPC476571
0.8679	High Similarity	NPC246587
0.8679	High Similarity	NPC428
0.8675	High Similarity	NPC167546
0.8675	High Similarity	NPC209377
0.8675	High Similarity	NPC225774
0.8675	High Similarity	NPC16805
0.8675	High Similarity	NPC302527
0.8671	High Similarity	NPC156576
0.8625	High Similarity	NPC103379
0.8625	High Similarity	NPC477565
0.8623	High Similarity	NPC13916
0.8623	High Similarity	NPC264850
0.8616	High Similarity	NPC179825
0.8616	High Similarity	NPC191376
0.8616	High Similarity	NPC321505
0.8613	High Similarity	NPC275132
0.8605	High Similarity	NPC126284
0.8598	High Similarity	NPC79328
0.8588	High Similarity	NPC478093
0.858	High Similarity	NPC82763
0.8571	High Similarity	NPC192768
0.8571	High Similarity	NPC88249
0.8571	High Similarity	NPC97221
0.8571	High Similarity	NPC220858
0.8571	High Similarity	NPC210918
0.8571	High Similarity	NPC151895
0.8563	High Similarity	NPC4138
0.8563	High Similarity	NPC284183
0.8563	High Similarity	NPC121275
0.8563	High Similarity	NPC24465
0.8544	High Similarity	NPC294249
0.8539	High Similarity	NPC473589
0.8539	High Similarity	NPC256124
0.8539	High Similarity	NPC478091
0.8539	High Similarity	NPC478092
0.8539	High Similarity	NPC30182
0.8537	High Similarity	NPC186063
0.8537	High Similarity	NPC29647
0.8529	High Similarity	NPC108434
0.8529	High Similarity	NPC475215
0.8529	High Similarity	NPC231371
0.85	High Similarity	NPC476151
0.8497	Intermediate Similarity	NPC32154
0.8494	Intermediate Similarity	NPC306902
0.8494	Intermediate Similarity	NPC232924
0.8494	Intermediate Similarity	NPC160298
0.8494	Intermediate Similarity	NPC266753
0.8494	Intermediate Similarity	NPC477559
0.8491	Intermediate Similarity	NPC185838
0.8476	Intermediate Similarity	NPC244112
0.8475	Intermediate Similarity	NPC175890
0.8475	Intermediate Similarity	NPC274661
0.8475	Intermediate Similarity	NPC11296
0.8475	Intermediate Similarity	NPC82457
0.8475	Intermediate Similarity	NPC48490
0.8466	Intermediate Similarity	NPC320088
0.8462	Intermediate Similarity	NPC150879
0.8462	Intermediate Similarity	NPC210140
0.8443	Intermediate Similarity	NPC80759
0.8443	Intermediate Similarity	NPC79402
0.8434	Intermediate Similarity	NPC7393
0.8427	Intermediate Similarity	NPC191132
0.8427	Intermediate Similarity	NPC60295
0.8421	Intermediate Similarity	NPC149090
0.8421	Intermediate Similarity	NPC19520
0.8418	Intermediate Similarity	NPC275680
0.8418	Intermediate Similarity	NPC22115
0.8412	Intermediate Similarity	NPC83198
0.8412	Intermediate Similarity	NPC204908
0.8402	Intermediate Similarity	NPC124657
0.8383	Intermediate Similarity	NPC230956
0.8383	Intermediate Similarity	NPC119649
0.8383	Intermediate Similarity	NPC271388
0.8383	Intermediate Similarity	NPC205255
0.8383	Intermediate Similarity	NPC235143
0.8382	Intermediate Similarity	NPC241704
0.8372	Intermediate Similarity	NPC232386
0.8372	Intermediate Similarity	NPC190783
0.8372	Intermediate Similarity	NPC152680
0.8362	Intermediate Similarity	NPC214116
0.8354	Intermediate Similarity	NPC26601
0.8352	Intermediate Similarity	NPC33902
0.8352	Intermediate Similarity	NPC276674
0.8343	Intermediate Similarity	NPC276944
0.8343	Intermediate Similarity	NPC232514

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 NPC477020 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	666
0.2-0.3	1097
0.3-0.4	1993
0.4-0.5	2661
0.5-0.6	1744
0.6-0.7	667
0.7-0.8	146
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
0.8553	High Similarity	NPD2421	Approved
0.8553	High Similarity	NPD2420	Approved
0.8491	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD3845	Phase 1
0.8304	Intermediate Similarity	NPD27	Approved
0.8304	Intermediate Similarity	NPD2489	Approved
0.8294	Intermediate Similarity	NPD3051	Approved
0.8272	Intermediate Similarity	NPD4584	Approved
0.8258	Intermediate Similarity	NPD7906	Approved
0.8246	Intermediate Similarity	NPD2969	Approved
0.8246	Intermediate Similarity	NPD2970	Approved
0.8239	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8192	Intermediate Similarity	NPD8053	Approved
0.8192	Intermediate Similarity	NPD8054	Approved
0.8182	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7298	Approved
0.8136	Intermediate Similarity	NPD4577	Approved
0.8136	Intermediate Similarity	NPD7311	Approved
0.8136	Intermediate Similarity	NPD7313	Approved
0.8136	Intermediate Similarity	NPD7312	Approved
0.8136	Intermediate Similarity	NPD4578	Approved
0.8136	Intermediate Similarity	NPD7310	Approved
0.8107	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD4663	Approved
0.809	Intermediate Similarity	NPD7309	Approved
0.8061	Intermediate Similarity	NPD6031	Approved
0.8061	Intermediate Similarity	NPD6030	Approved
0.8	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD2898	Approved
0.7988	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD2977	Approved
0.7882	Intermediate Similarity	NPD2978	Approved
0.7874	Intermediate Similarity	NPD4010	Discontinued
0.7866	Intermediate Similarity	NPD5241	Discontinued
0.7861	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3060	Approved
0.7797	Intermediate Similarity	NPD8251	Approved
0.7797	Intermediate Similarity	NPD8252	Approved
0.7797	Intermediate Similarity	NPD8099	Discontinued
0.7784	Intermediate Similarity	NPD4481	Phase 3
0.7772	Intermediate Similarity	NPD2490	Approved
0.7772	Intermediate Similarity	NPD2488	Approved
0.7753	Intermediate Similarity	NPD8156	Discontinued
0.7753	Intermediate Similarity	NPD42	Phase 2
0.7753	Intermediate Similarity	NPD6042	Phase 2
0.7746	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7831	Phase 2
0.7746	Intermediate Similarity	NPD7833	Phase 2
0.7735	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6788	Approved
0.7684	Intermediate Similarity	NPD3450	Approved
0.7684	Intermediate Similarity	NPD2493	Approved
0.7684	Intermediate Similarity	NPD3452	Approved
0.7684	Intermediate Similarity	NPD2494	Approved
0.7667	Intermediate Similarity	NPD6297	Approved
0.7657	Intermediate Similarity	NPD4666	Phase 3
0.7647	Intermediate Similarity	NPD4017	Approved
0.7619	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1424	Approved
0.7619	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5709	Phase 3
0.7574	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6071	Discontinued
0.7565	Intermediate Similarity	NPD4582	Approved
0.7565	Intermediate Similarity	NPD4583	Approved
0.7558	Intermediate Similarity	NPD4773	Phase 2
0.7558	Intermediate Similarity	NPD4772	Phase 2
0.7545	Intermediate Similarity	NPD5160	Discontinued
0.7529	Intermediate Similarity	NPD2560	Approved
0.7529	Intermediate Similarity	NPD2563	Approved
0.7529	Intermediate Similarity	NPD5976	Discontinued
0.7529	Intermediate Similarity	NPD4727	Phase 1
0.7513	Intermediate Similarity	NPD4002	Approved
0.7513	Intermediate Similarity	NPD4004	Approved
0.75	Intermediate Similarity	NPD6851	Approved
0.75	Intermediate Similarity	NPD6853	Approved
0.7485	Intermediate Similarity	NPD823	Approved
0.7485	Intermediate Similarity	NPD817	Approved
0.7474	Intermediate Similarity	NPD2973	Approved
0.7474	Intermediate Similarity	NPD2975	Approved
0.7474	Intermediate Similarity	NPD4040	Phase 1
0.7474	Intermediate Similarity	NPD2974	Approved
0.7469	Intermediate Similarity	NPD3109	Approved
0.7469	Intermediate Similarity	NPD3110	Approved
0.7468	Intermediate Similarity	NPD3053	Approved
0.7468	Intermediate Similarity	NPD3055	Approved
0.7456	Intermediate Similarity	NPD7598	Phase 2
0.7446	Intermediate Similarity	NPD2968	Approved
0.7446	Intermediate Similarity	NPD2971	Approved
0.7443	Intermediate Similarity	NPD4055	Discovery
0.744	Intermediate Similarity	NPD2677	Approved
0.7427	Intermediate Similarity	NPD3641	Approved
0.7427	Intermediate Similarity	NPD3640	Phase 3
0.7427	Intermediate Similarity	NPD3639	Approved
0.7425	Intermediate Similarity	NPD4162	Approved
0.7421	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7479	Phase 2
0.7416	Intermediate Similarity	NPD6107	Approved
0.7394	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7827	Phase 1
0.7381	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4257	Approved
0.7365	Intermediate Similarity	NPD4256	Phase 2
0.7363	Intermediate Similarity	NPD4873	Discontinued
0.7363	Intermediate Similarity	NPD7047	Phase 3
0.7362	Intermediate Similarity	NPD3059	Approved
0.7362	Intermediate Similarity	NPD3062	Approved
0.7362	Intermediate Similarity	NPD3061	Approved
0.7358	Intermediate Similarity	NPD4580	Approved
0.7346	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5177	Phase 3
0.7317	Intermediate Similarity	NPD6997	Phase 2
0.7301	Intermediate Similarity	NPD1132	Approved
0.7301	Intermediate Similarity	NPD1136	Approved
0.7301	Intermediate Similarity	NPD1130	Approved
0.7301	Intermediate Similarity	NPD2674	Phase 3
0.7289	Intermediate Similarity	NPD1753	Discontinued
0.7284	Intermediate Similarity	NPD5156	Approved
0.7284	Intermediate Similarity	NPD5155	Approved
0.7278	Intermediate Similarity	NPD4166	Phase 2
0.7273	Intermediate Similarity	NPD4585	Approved
0.7273	Intermediate Similarity	NPD5314	Approved
0.7267	Intermediate Similarity	NPD6090	Discontinued
0.7253	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7922	Phase 1
0.7241	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD601	Approved
0.7239	Intermediate Similarity	NPD598	Approved
0.7239	Intermediate Similarity	NPD5718	Phase 2
0.7239	Intermediate Similarity	NPD597	Approved
0.7238	Intermediate Similarity	NPD4083	Discontinued
0.7235	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2606	Approved
0.7222	Intermediate Similarity	NPD3594	Approved
0.7222	Intermediate Similarity	NPD2605	Approved
0.7222	Intermediate Similarity	NPD7802	Discontinued
0.7222	Intermediate Similarity	NPD3595	Approved
0.7202	Intermediate Similarity	NPD4721	Approved
0.7202	Intermediate Similarity	NPD4725	Approved
0.7202	Intermediate Similarity	NPD4726	Approved
0.7193	Intermediate Similarity	NPD3122	Phase 3
0.7188	Intermediate Similarity	NPD5310	Approved
0.7188	Intermediate Similarity	NPD5311	Approved
0.7186	Intermediate Similarity	NPD2155	Approved
0.7186	Intermediate Similarity	NPD2154	Approved
0.7186	Intermediate Similarity	NPD2156	Approved
0.7184	Intermediate Similarity	NPD3687	Approved
0.7184	Intermediate Similarity	NPD3686	Approved
0.7179	Intermediate Similarity	NPD6612	Phase 2
0.7178	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3636	Approved
0.716	Intermediate Similarity	NPD3637	Approved
0.716	Intermediate Similarity	NPD3635	Approved
0.7159	Intermediate Similarity	NPD6072	Discontinued
0.7151	Intermediate Similarity	NPD7038	Approved
0.7151	Intermediate Similarity	NPD1774	Approved
0.7151	Intermediate Similarity	NPD7039	Approved
0.7143	Intermediate Similarity	NPD4005	Discontinued
0.7143	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3145	Approved
0.7134	Intermediate Similarity	NPD3144	Approved
0.7128	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3645	Discontinued
0.711	Intermediate Similarity	NPD4123	Phase 3
0.7107	Intermediate Similarity	NPD2491	Approved
0.7107	Intermediate Similarity	NPD3448	Approved
0.7107	Intermediate Similarity	NPD3057	Approved
0.7091	Intermediate Similarity	NPD4474	Approved
0.7091	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4475	Approved
0.7089	Intermediate Similarity	NPD6723	Discontinued
0.7081	Intermediate Similarity	NPD5095	Phase 3
0.7081	Intermediate Similarity	NPD5096	Phase 3
0.7081	Intermediate Similarity	NPD3933	Discontinued
0.7068	Intermediate Similarity	NPD2845	Phase 2
0.7068	Intermediate Similarity	NPD2843	Phase 2
0.7066	Intermediate Similarity	NPD3052	Approved
0.7066	Intermediate Similarity	NPD3054	Approved
0.7052	Intermediate Similarity	NPD3124	Discontinued
0.7041	Intermediate Similarity	NPD8095	Phase 1
0.7037	Intermediate Similarity	NPD6618	Phase 2
0.7027	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6896	Approved
0.7024	Intermediate Similarity	NPD6895	Approved
0.7022	Intermediate Similarity	NPD5720	Discontinued
0.702	Intermediate Similarity	NPD2972	Approved
0.702	Intermediate Similarity	NPD3533	Approved
0.7018	Intermediate Similarity	NPD4237	Approved
0.7018	Intermediate Similarity	NPD4236	Phase 3
0.7012	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3536	Discontinued
0.6994	Remote Similarity	NPD2194	Approved
0.6994	Remote Similarity	NPD9619	Approved
0.6994	Remote Similarity	NPD9621	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