NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	638.3
Volume:	657.796
LogP:	5.277
LogD:	3.777
LogS:	-3.687
# Rotatable Bonds:	8
TPSA:	93.09
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.226
Synthetic Accessibility Score:	3.952
Fsp3:	0.368
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.658
MDCK Permeability:	2.672202572284732e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.346
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.901

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	77.90634155273438%
Volume Distribution (VD):	1.113
Pgp-substrate:	19.692068099975586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.598
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.953
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.951

ADMET: Excretion

Clearance (CL):	8.89
Half-life (T1/2):	0.367

ADMET: Toxicity

hERG Blockers:	0.948
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.561
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.453
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.848
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.356

Download Data

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

Natural Product: NPC478093

Natural Product ID:	NPC478093
*Common Name:**	(6aR)-8-[4-[[(1S)-6-hydroxy-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]phenoxy]-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-9-ol
IUPAC Name:	(6aR)-8-[4-[[(1S)-6-hydroxy-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]phenoxy]-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-9-ol
Synonyms:
Standard InCHIKey:	RRRBUQLZAIRJQZ-URLMMPGGSA-N
Standard InCHI:	InChI=1S/C38H42N2O7/c1-39-13-11-22-16-30(41)31(43-3)19-25(22)28(39)15-21-7-9-24(10-8-21)47-37-27-18-29-34-23(12-14-40(29)2)17-33(45-5)38(46-6)35(34)26(27)20-32(44-4)36(37)42/h7-10,16-17,19-20,28-29,41-42H,11-15,18H2,1-6H3/t28-,29+/m0/s1
SMILES:	CN1CCC2=CC(=C(C3=C2[C@H]1CC4=C(C(=C(C=C43)OC)O)OC5=CC=C(C=C5)C[C@H]6C7=CC(=C(C=C7CCN6C)O)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49799720
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
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[19299148]
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7528786]
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	11200	ug/ml	PMID[19299148]

☑ 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 NPC478093 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	376
0.1-0.2	1759
0.2-0.3	8345
0.3-0.4	10050
0.4-0.5	5227
0.5-0.6	8636
0.6-0.7	6728
0.7-0.8	1213
0.8-0.85	180
0.85-0.9	93
0.9-0.95	73
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9942	High Similarity	NPC478092
0.9942	High Similarity	NPC30182
0.9942	High Similarity	NPC478091
0.9942	High Similarity	NPC473589
0.9595	High Similarity	NPC22115
0.9595	High Similarity	NPC275680
0.9535	High Similarity	NPC302275
0.9532	High Similarity	NPC286119
0.948	High Similarity	NPC95426
0.948	High Similarity	NPC302245
0.948	High Similarity	NPC16357
0.9477	High Similarity	NPC8836
0.9477	High Similarity	NPC7715
0.9477	High Similarity	NPC271013
0.9477	High Similarity	NPC222661
0.9477	High Similarity	NPC182052
0.9477	High Similarity	NPC90998
0.9477	High Similarity	NPC239824
0.9477	High Similarity	NPC181796
0.9477	High Similarity	NPC328155
0.9477	High Similarity	NPC279228
0.9477	High Similarity	NPC251735
0.9477	High Similarity	NPC258657
0.9477	High Similarity	NPC223690
0.9477	High Similarity	NPC229373
0.9477	High Similarity	NPC185639
0.9477	High Similarity	NPC15414
0.9477	High Similarity	NPC54654
0.9477	High Similarity	NPC285931
0.9477	High Similarity	NPC290005
0.9477	High Similarity	NPC42663
0.9477	High Similarity	NPC290582
0.9477	High Similarity	NPC104196
0.9477	High Similarity	NPC217748
0.9477	High Similarity	NPC49075
0.9477	High Similarity	NPC311973
0.9477	High Similarity	NPC30779
0.9429	High Similarity	NPC206900
0.9425	High Similarity	NPC139783
0.9425	High Similarity	NPC65312
0.9422	High Similarity	NPC167116
0.9422	High Similarity	NPC274716
0.9422	High Similarity	NPC254441
0.9314	High Similarity	NPC116465
0.9314	High Similarity	NPC14507
0.9314	High Similarity	NPC47077
0.9314	High Similarity	NPC212237
0.9209	High Similarity	NPC175890
0.9209	High Similarity	NPC274661
0.9209	High Similarity	NPC48490
0.9209	High Similarity	NPC11296
0.9209	High Similarity	NPC82457
0.9181	High Similarity	NPC239775
0.9162	High Similarity	NPC256124
0.9157	High Similarity	NPC60295
0.9157	High Similarity	NPC191132
0.9123	High Similarity	NPC118274
0.9123	High Similarity	NPC168753
0.9106	High Similarity	NPC24260
0.907	High Similarity	NPC317439
0.907	High Similarity	NPC115284
0.907	High Similarity	NPC63646
0.907	High Similarity	NPC76682
0.907	High Similarity	NPC276890
0.907	High Similarity	NPC227060
0.907	High Similarity	NPC10908
0.907	High Similarity	NPC317145
0.907	High Similarity	NPC198498
0.9017	High Similarity	NPC41376
0.9017	High Similarity	NPC12424
0.9017	High Similarity	NPC251580
0.9017	High Similarity	NPC129518
0.8947	High Similarity	NPC317272
0.8947	High Similarity	NPC42549
0.8947	High Similarity	NPC240841
0.8947	High Similarity	NPC256012
0.8947	High Similarity	NPC250846
0.8947	High Similarity	NPC268503
0.8944	High Similarity	NPC318805
0.8944	High Similarity	NPC41122
0.892	High Similarity	NPC474507
0.8914	High Similarity	NPC293093
0.8895	High Similarity	NPC145832
0.8895	High Similarity	NPC12053
0.8895	High Similarity	NPC117188
0.8895	High Similarity	NPC205421
0.8895	High Similarity	NPC474931
0.8895	High Similarity	NPC81218
0.8895	High Similarity	NPC306555
0.8895	High Similarity	NPC158376
0.8889	High Similarity	NPC196447
0.8889	High Similarity	NPC253043
0.8889	High Similarity	NPC78222
0.8889	High Similarity	NPC477563
0.8889	High Similarity	NPC96603
0.8889	High Similarity	NPC306843
0.8889	High Similarity	NPC212794
0.8889	High Similarity	NPC13504
0.8889	High Similarity	NPC136508
0.8852	High Similarity	NPC234318
0.8846	High Similarity	NPC85381
0.8837	High Similarity	NPC264850
0.8837	High Similarity	NPC13916
0.883	High Similarity	NPC324144
0.8814	High Similarity	NPC243454
0.8814	High Similarity	NPC475479
0.8811	High Similarity	NPC475654
0.8807	High Similarity	NPC173416
0.8807	High Similarity	NPC476577
0.8807	High Similarity	NPC148709
0.8779	High Similarity	NPC24465
0.877	High Similarity	NPC254581
0.8764	High Similarity	NPC239584
0.8736	High Similarity	NPC204908
0.8736	High Similarity	NPC83198
0.8721	High Similarity	NPC1229
0.8715	High Similarity	NPC73492
0.8715	High Similarity	NPC299990
0.8713	High Similarity	NPC166014
0.8713	High Similarity	NPC27410
0.8636	High Similarity	NPC475215
0.8636	High Similarity	NPC108434
0.8588	High Similarity	NPC66341
0.8588	High Similarity	NPC477020
0.8588	High Similarity	NPC232386
0.8588	High Similarity	NPC192135
0.8588	High Similarity	NPC152680
0.8588	High Similarity	NPC190783
0.858	High Similarity	NPC26240
0.858	High Similarity	NPC477562
0.858	High Similarity	NPC69712
0.8579	High Similarity	NPC82763
0.8556	High Similarity	NPC195538
0.8556	High Similarity	NPC257269
0.8556	High Similarity	NPC230276
0.8555	High Similarity	NPC60186
0.8547	High Similarity	NPC320223
0.8547	High Similarity	NPC114364
0.8539	High Similarity	NPC128560
0.8539	High Similarity	NPC199465
0.8539	High Similarity	NPC229166
0.8538	High Similarity	NPC247639
0.8538	High Similarity	NPC25084
0.8525	High Similarity	NPC476576
0.8525	High Similarity	NPC186546
0.8516	High Similarity	NPC249996
0.8508	High Similarity	NPC476202
0.85	High Similarity	NPC40496
0.85	High Similarity	NPC119068
0.8497	Intermediate Similarity	NPC119649
0.8497	Intermediate Similarity	NPC230956
0.8497	Intermediate Similarity	NPC271388
0.8497	Intermediate Similarity	NPC205255
0.8497	Intermediate Similarity	NPC235143
0.8488	Intermediate Similarity	NPC476572
0.848	Intermediate Similarity	NPC325871
0.848	Intermediate Similarity	NPC99659
0.8478	Intermediate Similarity	NPC281581
0.8466	Intermediate Similarity	NPC204947
0.8448	Intermediate Similarity	NPC80759
0.8448	Intermediate Similarity	NPC79402
0.8439	Intermediate Similarity	NPC221864
0.8432	Intermediate Similarity	NPC475597
0.8432	Intermediate Similarity	NPC473716
0.8427	Intermediate Similarity	NPC149090
0.8427	Intermediate Similarity	NPC19520
0.8409	Intermediate Similarity	NPC476573
0.8409	Intermediate Similarity	NPC35627
0.8409	Intermediate Similarity	NPC81247
0.8384	Intermediate Similarity	NPC82056
0.8372	Intermediate Similarity	NPC189266
0.8372	Intermediate Similarity	NPC2413
0.8372	Intermediate Similarity	NPC127674
0.8372	Intermediate Similarity	NPC204828
0.8372	Intermediate Similarity	NPC249797
0.8372	Intermediate Similarity	NPC295691
0.8372	Intermediate Similarity	NPC184026
0.8372	Intermediate Similarity	NPC5238
0.8372	Intermediate Similarity	NPC172765
0.8372	Intermediate Similarity	NPC276588
0.8372	Intermediate Similarity	NPC207757
0.8372	Intermediate Similarity	NPC278799
0.8372	Intermediate Similarity	NPC193949
0.8372	Intermediate Similarity	NPC469817
0.8372	Intermediate Similarity	NPC110416
0.8372	Intermediate Similarity	NPC39701
0.8372	Intermediate Similarity	NPC54379
0.837	Intermediate Similarity	NPC57036
0.837	Intermediate Similarity	NPC214116
0.8333	Intermediate Similarity	NPC475754
0.8324	Intermediate Similarity	NPC231371
0.8306	Intermediate Similarity	NPC116284
0.8304	Intermediate Similarity	NPC81733
0.8304	Intermediate Similarity	NPC326316
0.8297	Intermediate Similarity	NPC32154
0.8295	Intermediate Similarity	NPC475393
0.8283	Intermediate Similarity	NPC38964
0.8266	Intermediate Similarity	NPC123323
0.8261	Intermediate Similarity	NPC135772
0.8258	Intermediate Similarity	NPC298979

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 NPC478093 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	802
0.2-0.3	1174
0.3-0.4	2226
0.4-0.5	2384
0.5-0.6	1560
0.6-0.7	629
0.7-0.8	128
0.8-0.85	23
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9477	High Similarity	NPD8054	Approved
0.9477	High Similarity	NPD8053	Approved
0.907	High Similarity	NPD8252	Approved
0.907	High Similarity	NPD8251	Approved
0.907	High Similarity	NPD8099	Discontinued
0.9017	High Similarity	NPD8156	Discontinued
0.85	High Similarity	NPD8453	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD7906	Approved
0.8168	Intermediate Similarity	NPD8095	Phase 1
0.8152	Intermediate Similarity	NPD7312	Approved
0.8152	Intermediate Similarity	NPD7310	Approved
0.8152	Intermediate Similarity	NPD7311	Approved
0.8152	Intermediate Similarity	NPD7313	Approved
0.8111	Intermediate Similarity	NPD2489	Approved
0.8111	Intermediate Similarity	NPD27	Approved
0.8108	Intermediate Similarity	NPD7309	Approved
0.8101	Intermediate Similarity	NPD3051	Approved
0.8056	Intermediate Similarity	NPD2970	Approved
0.8056	Intermediate Similarity	NPD2969	Approved
0.8054	Intermediate Similarity	NPD4577	Approved
0.8054	Intermediate Similarity	NPD4578	Approved
0.8021	Intermediate Similarity	NPD4663	Approved
0.8012	Intermediate Similarity	NPD2421	Approved
0.8012	Intermediate Similarity	NPD2420	Approved
0.7965	Intermediate Similarity	NPD4584	Approved
0.7921	Intermediate Similarity	NPD6788	Approved
0.7877	Intermediate Similarity	NPD7831	Phase 2
0.7877	Intermediate Similarity	NPD7833	Phase 2
0.7877	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6071	Discontinued
0.7697	Intermediate Similarity	NPD4773	Phase 2
0.7697	Intermediate Similarity	NPD4772	Phase 2
0.7654	Intermediate Similarity	NPD7298	Approved
0.7626	Intermediate Similarity	NPD3452	Approved
0.7626	Intermediate Similarity	NPD2494	Approved
0.7626	Intermediate Similarity	NPD2493	Approved
0.7626	Intermediate Similarity	NPD3450	Approved
0.7622	Intermediate Similarity	NPD4481	Phase 3
0.7617	Intermediate Similarity	NPD2488	Approved
0.7617	Intermediate Similarity	NPD2490	Approved
0.7596	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7447	Phase 1
0.7557	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD2898	Approved
0.7524	Intermediate Similarity	NPD6997	Phase 2
0.7512	Intermediate Similarity	NPD4583	Approved
0.7512	Intermediate Similarity	NPD4582	Approved
0.7488	Intermediate Similarity	NPD7047	Phase 3
0.7473	Intermediate Similarity	NPD2560	Approved
0.7473	Intermediate Similarity	NPD2563	Approved
0.7463	Intermediate Similarity	NPD4002	Approved
0.7463	Intermediate Similarity	NPD4004	Approved
0.7443	Intermediate Similarity	NPD3845	Phase 1
0.7424	Intermediate Similarity	NPD2974	Approved
0.7424	Intermediate Similarity	NPD2973	Approved
0.7424	Intermediate Similarity	NPD2975	Approved
0.7419	Intermediate Similarity	NPD4010	Discontinued
0.7401	Intermediate Similarity	NPD7212	Phase 2
0.7401	Intermediate Similarity	NPD7213	Phase 3
0.7391	Intermediate Similarity	NPD4055	Discovery
0.7386	Intermediate Similarity	NPD5241	Discontinued
0.7345	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7549	Discontinued
0.7341	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4580	Approved
0.7306	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD2968	Approved
0.7306	Intermediate Similarity	NPD2971	Approved
0.7288	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6031	Approved
0.7278	Intermediate Similarity	NPD6030	Approved
0.7268	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1424	Approved
0.726	Intermediate Similarity	NPD7827	Phase 1
0.7253	Intermediate Similarity	NPD4678	Approved
0.7253	Intermediate Similarity	NPD4675	Approved
0.7247	Intermediate Similarity	NPD7124	Phase 2
0.7225	Intermediate Similarity	NPD42	Phase 2
0.7225	Intermediate Similarity	NPD6042	Phase 2
0.7219	Intermediate Similarity	NPD5677	Discontinued
0.7213	Intermediate Similarity	NPD6072	Discontinued
0.7198	Intermediate Similarity	NPD4017	Approved
0.7182	Intermediate Similarity	NPD3639	Approved
0.7182	Intermediate Similarity	NPD3641	Approved
0.7182	Intermediate Similarity	NPD3640	Phase 3
0.7181	Intermediate Similarity	NPD7802	Discontinued
0.7181	Intermediate Similarity	NPD8153	Approved
0.7181	Intermediate Similarity	NPD8152	Approved
0.7171	Intermediate Similarity	NPD4040	Phase 1
0.715	Intermediate Similarity	NPD7907	Approved
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD6090	Discontinued
0.7111	Intermediate Similarity	NPD7598	Phase 2
0.7104	Intermediate Similarity	NPD4005	Discontinued
0.709	Intermediate Similarity	NPD6107	Approved
0.7062	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4475	Approved
0.7052	Intermediate Similarity	NPD4474	Approved
0.7048	Intermediate Similarity	NPD5676	Approved
0.7021	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3109	Approved
0.7011	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3110	Approved
0.701	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2122	Discontinued
0.6994	Remote Similarity	NPD5718	Phase 2
0.6994	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3448	Approved
0.699	Remote Similarity	NPD2491	Approved
0.699	Remote Similarity	NPD3057	Approved
0.6989	Remote Similarity	NPD2200	Suspended
0.6983	Remote Similarity	NPD5177	Phase 3
0.6982	Remote Similarity	NPD6723	Discontinued
0.6978	Remote Similarity	NPD4123	Phase 3
0.6977	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7048	Phase 3
0.6961	Remote Similarity	NPD6667	Approved
0.6961	Remote Similarity	NPD6666	Approved
0.6952	Remote Similarity	NPD5773	Approved
0.6952	Remote Similarity	NPD5772	Approved
0.6952	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4666	Phase 3
0.6944	Remote Similarity	NPD7466	Approved
0.6944	Remote Similarity	NPD6748	Discontinued
0.6943	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4625	Phase 3
0.6931	Remote Similarity	NPD7262	Phase 1
0.6927	Remote Similarity	NPD7037	Approved
0.6927	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3124	Discontinued
0.6923	Remote Similarity	NPD7479	Phase 2
0.6919	Remote Similarity	NPD6851	Approved
0.6919	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6853	Approved
0.6919	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1613	Approved
0.6912	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.691	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5005	Approved
0.6908	Remote Similarity	NPD5006	Approved
0.6908	Remote Similarity	NPD2972	Approved
0.6908	Remote Similarity	NPD3533	Approved
0.6907	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD4111	Phase 1
0.6898	Remote Similarity	NPD4665	Approved
0.6897	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5709	Phase 3
0.6893	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6297	Approved
0.6885	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4908	Phase 1
0.6872	Remote Similarity	NPD5312	Approved
0.6872	Remote Similarity	NPD5313	Approved
0.6872	Remote Similarity	NPD4873	Discontinued
0.6854	Remote Similarity	NPD1753	Discontinued
0.6853	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7169	Suspended
0.6848	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5155	Approved
0.6839	Remote Similarity	NPD5156	Approved
0.6833	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.683	Remote Similarity	NPD7922	Phase 1
0.6821	Remote Similarity	NPD7177	Discontinued
0.6818	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7291	Discontinued
0.6813	Remote Similarity	NPD5160	Discontinued
0.6813	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3692	Discontinued
0.6811	Remote Similarity	NPD5976	Discontinued
0.6809	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6896	Approved
0.6798	Remote Similarity	NPD6895	Approved
0.6798	Remote Similarity	NPD6111	Discontinued
0.6796	Remote Similarity	NPD3060	Approved
0.6796	Remote Similarity	NPD4420	Approved
0.6788	Remote Similarity	NPD4166	Phase 2
0.6782	Remote Similarity	NPD3594	Approved
0.6782	Remote Similarity	NPD2605	Approved
0.6782	Remote Similarity	NPD3595	Approved
0.6782	Remote Similarity	NPD2606	Approved
0.6778	Remote Similarity	NPD4725	Approved
0.6778	Remote Similarity	NPD4721	Approved
0.6778	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4726	Approved
0.6776	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4585	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