NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	538.2
Volume:	555.243
LogP:	5.358
LogD:	4.333
LogS:	-3.981
# Rotatable Bonds:	6
TPSA:	86.61
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.279
Synthetic Accessibility Score:	4.111
Fsp3:	0.212
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.121
MDCK Permeability:	3.061281313421205e-05
Pgp-inhibitor:	0.851
Pgp-substrate:	0.736
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	91.2698745727539%
Volume Distribution (VD):	0.545
Pgp-substrate:	6.2001953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.133
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.974
CYP2C19-substrate:	0.665
CYP2C9-inhibitor:	0.97
CYP2C9-substrate:	0.985
CYP2D6-inhibitor:	0.761
CYP2D6-substrate:	0.946
CYP3A4-inhibitor:	0.876
CYP3A4-substrate:	0.865

ADMET: Excretion

Clearance (CL):	6.658
Half-life (T1/2):	0.168

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.551
Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.205
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.184
Respiratory Toxicity:	0.59

Download Data

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

Natural Product: NPC476616

Natural Product ID:	NPC476616
*Common Name:**	(6S,6aR,7S,12aR)-1,8-dimethoxy-7-[(E)-2-(4-methoxyphenyl)ethenyl]-6-phenyl-6,6a,7,12a-tetrahydrochromeno[3,2-c]chromene-3,10-diol
IUPAC Name:	(6S,6aR,7S,12aR)-1,8-dimethoxy-7-[(E)-2-(4-methoxyphenyl)ethenyl]-6-phenyl-6,6a,7,12a-tetrahydrochromeno[3,2-c]chromene-3,10-diol
Synonyms:
Standard InCHIKey:	NTMAFGPMRMTODT-BIJDMMQYSA-N
Standard InCHI:	InChI=1S/C33H30O7/c1-36-23-12-9-19(10-13-23)11-14-24-29-25(37-2)15-21(34)17-27(29)40-33-30(24)32(20-7-5-4-6-8-20)39-28-18-22(35)16-26(38-3)31(28)33/h4-18,24,30,32-35H,1-3H3/b14-11+/t24-,30-,32-,33-/m1/s1
SMILES:	COc1ccc(cc1)/C=C/[C@@H]1c2c(cc(cc2O[C@@H]2[C@H]1[C@@H](c1ccccc1)Oc1cc(cc(c21)OC)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3291071
PubChem CID:	90682494
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-O-methylated flavonoids

*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
NPO33610	Arrabidaea brachypoda	Species	Bignoniaceae	Eukaryota	roots	SantAna da Serra farm Joo Pinheiro, Minas Gerais, Brazil	2010-APR	PMID[24871307]
NPO40516	Arrabidaea brachypoda	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32902988]

☑ 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	3
Others	5

Activity Type	# Activity
Individual Protein	1
Organism	4
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	5300.0	nM	PMID[506194]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	6000.0	nM	PMID[506194]
NPT27	Others	Unspecified		LC50	=	15600.0	nM	PMID[506194]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Inhibition	=	0.0	%	PMID[506194]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	92.0	%	PMID[506194]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	2200.0	nM	PMID[506195]
NPT2	Others	Unspecified		CC50	>	20000.0	nM	PMID[506195]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	9.1	n.a.	PMID[506195]

☑ 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 NPC476616 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	405
0.1-0.2	1542
0.2-0.3	3905
0.3-0.4	12190
0.4-0.5	6486
0.5-0.6	4519
0.6-0.7	7844
0.7-0.8	4767
0.8-0.85	669
0.85-0.9	241
0.9-0.95	115
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476617
1.0	High Similarity	NPC476615
0.9692	High Similarity	NPC471522
0.9618	High Similarity	NPC470308
0.9618	High Similarity	NPC470307
0.9338	High Similarity	NPC475492
0.9259	High Similarity	NPC100482
0.9259	High Similarity	NPC277331
0.9219	High Similarity	NPC26879
0.9219	High Similarity	NPC50315
0.9219	High Similarity	NPC283049
0.9219	High Similarity	NPC230479
0.9173	High Similarity	NPC11727
0.9173	High Similarity	NPC125579
0.9173	High Similarity	NPC15109
0.9134	High Similarity	NPC76465
0.9134	High Similarity	NPC38761
0.9104	High Similarity	NPC141717
0.9098	High Similarity	NPC473107
0.9077	High Similarity	NPC38664
0.9077	High Similarity	NPC47283
0.9077	High Similarity	NPC39064
0.9077	High Similarity	NPC53986
0.9055	High Similarity	NPC36016
0.9055	High Similarity	NPC100099
0.9023	High Similarity	NPC77196
0.9015	High Similarity	NPC129784
0.9015	High Similarity	NPC164804
0.9015	High Similarity	NPC471517
0.9015	High Similarity	NPC118114
0.9015	High Similarity	NPC473309
0.9015	High Similarity	NPC129106
0.9015	High Similarity	NPC196765
0.9015	High Similarity	NPC211413
0.9015	High Similarity	NPC268917
0.9015	High Similarity	NPC244888
0.9015	High Similarity	NPC207892
0.9015	High Similarity	NPC228369
0.9015	High Similarity	NPC236014
0.9015	High Similarity	NPC206224
0.9015	High Similarity	NPC164574
0.9015	High Similarity	NPC476166
0.9015	High Similarity	NPC293203
0.9015	High Similarity	NPC280653
0.9015	High Similarity	NPC17343
0.9015	High Similarity	NPC300875
0.9015	High Similarity	NPC118683
0.9015	High Similarity	NPC12875
0.9015	High Similarity	NPC68205
0.9015	High Similarity	NPC150011
0.9008	High Similarity	NPC93962
0.9008	High Similarity	NPC471519
0.9008	High Similarity	NPC471518
0.8992	High Similarity	NPC285040
0.8992	High Similarity	NPC188022
0.8992	High Similarity	NPC103420
0.8992	High Similarity	NPC102540
0.8992	High Similarity	NPC17809
0.8976	High Similarity	NPC193364
0.8976	High Similarity	NPC54972
0.8955	High Similarity	NPC97834
0.8955	High Similarity	NPC198154
0.8955	High Similarity	NPC296915
0.8955	High Similarity	NPC223008
0.8955	High Similarity	NPC225696
0.8955	High Similarity	NPC115335
0.8947	High Similarity	NPC13005
0.8939	High Similarity	NPC27187
0.8939	High Similarity	NPC470225
0.8931	High Similarity	NPC274717
0.8929	High Similarity	NPC102280
0.8929	High Similarity	NPC248053
0.8929	High Similarity	NPC155564
0.8923	High Similarity	NPC276212
0.8923	High Similarity	NPC471215
0.8923	High Similarity	NPC262573
0.8915	High Similarity	NPC86502
0.8915	High Similarity	NPC197351
0.8915	High Similarity	NPC106914
0.8915	High Similarity	NPC134195
0.8915	High Similarity	NPC246648
0.8906	High Similarity	NPC255026
0.8905	High Similarity	NPC213607
0.8905	High Similarity	NPC182509
0.8905	High Similarity	NPC174787
0.8873	High Similarity	NPC211561
0.8872	High Similarity	NPC181497
0.8872	High Similarity	NPC162801
0.8872	High Similarity	NPC271945
0.8865	High Similarity	NPC70409
0.8865	High Similarity	NPC18185
0.8865	High Similarity	NPC262911
0.8865	High Similarity	NPC294558
0.8865	High Similarity	NPC58190
0.8865	High Similarity	NPC236202
0.8865	High Similarity	NPC204770
0.8865	High Similarity	NPC202742
0.8865	High Similarity	NPC170103
0.8865	High Similarity	NPC108811
0.8865	High Similarity	NPC82917
0.8865	High Similarity	NPC263940
0.8857	High Similarity	NPC149633
0.8855	High Similarity	NPC149796
0.8832	High Similarity	NPC475836
0.8819	High Similarity	NPC93398
0.8819	High Similarity	NPC258979
0.8819	High Similarity	NPC8283
0.8811	High Similarity	NPC477612
0.8803	High Similarity	NPC281549
0.8797	High Similarity	NPC254000
0.8794	High Similarity	NPC71686
0.8794	High Similarity	NPC176804
0.8794	High Similarity	NPC96576
0.8794	High Similarity	NPC14468
0.8788	High Similarity	NPC222572
0.8788	High Similarity	NPC87224
0.8786	High Similarity	NPC28440
0.8786	High Similarity	NPC171932
0.8769	High Similarity	NPC294156
0.8769	High Similarity	NPC256015
0.8768	High Similarity	NPC22317
0.876	High Similarity	NPC174977
0.875	High Similarity	NPC259707
0.875	High Similarity	NPC471403
0.8741	High Similarity	NPC321657
0.8741	High Similarity	NPC318373
0.8741	High Similarity	NPC92805
0.8741	High Similarity	NPC85435
0.8741	High Similarity	NPC469610
0.874	High Similarity	NPC172253
0.874	High Similarity	NPC59561
0.8732	High Similarity	NPC6702
0.8732	High Similarity	NPC111134
0.8732	High Similarity	NPC242774
0.8732	High Similarity	NPC237546
0.8732	High Similarity	NPC133209
0.8732	High Similarity	NPC224921
0.8732	High Similarity	NPC231712
0.8732	High Similarity	NPC112819
0.8731	High Similarity	NPC103799
0.8731	High Similarity	NPC472590
0.8731	High Similarity	NPC8899
0.8723	High Similarity	NPC43716
0.8723	High Similarity	NPC101255
0.8723	High Similarity	NPC475719
0.8722	High Similarity	NPC134360
0.8714	High Similarity	NPC173203
0.8714	High Similarity	NPC163508
0.8705	High Similarity	NPC178054
0.8702	High Similarity	NPC113495
0.869	High Similarity	NPC226809
0.869	High Similarity	NPC279406
0.8686	High Similarity	NPC20829
0.8686	High Similarity	NPC18189
0.8686	High Similarity	NPC262585
0.8676	High Similarity	NPC124085
0.8676	High Similarity	NPC117048
0.8671	High Similarity	NPC227516
0.8671	High Similarity	NPC20757
0.8667	High Similarity	NPC469611
0.8652	High Similarity	NPC15659
0.8652	High Similarity	NPC304894
0.8633	High Similarity	NPC262189
0.863	High Similarity	NPC224161
0.8623	High Similarity	NPC474687
0.8623	High Similarity	NPC472646
0.8623	High Similarity	NPC211549
0.8623	High Similarity	NPC71465
0.8613	High Similarity	NPC37410
0.8613	High Similarity	NPC258780
0.8611	High Similarity	NPC122980
0.8611	High Similarity	NPC476969
0.8611	High Similarity	NPC148516
0.8611	High Similarity	NPC180605
0.8611	High Similarity	NPC107862
0.8611	High Similarity	NPC177172
0.8603	High Similarity	NPC11060
0.8601	High Similarity	NPC174251
0.8601	High Similarity	NPC153182
0.8594	High Similarity	NPC295259
0.8593	High Similarity	NPC238168
0.8593	High Similarity	NPC282508
0.8593	High Similarity	NPC237424
0.8582	High Similarity	NPC222108
0.8582	High Similarity	NPC96719
0.8571	High Similarity	NPC473134
0.8571	High Similarity	NPC46335
0.8571	High Similarity	NPC5155
0.8562	High Similarity	NPC44192
0.8562	High Similarity	NPC469944
0.8562	High Similarity	NPC59692
0.8562	High Similarity	NPC233467
0.8562	High Similarity	NPC226108
0.8562	High Similarity	NPC272552
0.8562	High Similarity	NPC134911
0.8562	High Similarity	NPC46283
0.8562	High Similarity	NPC322899
0.8561	High Similarity	NPC167571
0.8561	High Similarity	NPC278552
0.8561	High Similarity	NPC471388

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 NPC476616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	927
0.2-0.3	1580
0.3-0.4	2682
0.4-0.5	1773
0.5-0.6	1065
0.6-0.7	646
0.7-0.8	125
0.8-0.85	13
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9528	High Similarity	NPD4908	Phase 1
0.938	High Similarity	NPD4907	Clinical (unspecified phase)
0.8976	High Similarity	NPD1610	Phase 2
0.8516	High Similarity	NPD1548	Phase 1
0.8333	Intermediate Similarity	NPD7212	Phase 2
0.8333	Intermediate Similarity	NPD7213	Phase 3
0.8296	Intermediate Similarity	NPD2861	Phase 2
0.8276	Intermediate Similarity	NPD7447	Phase 1
0.8271	Intermediate Similarity	NPD4749	Approved
0.8261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD1613	Approved
0.8175	Intermediate Similarity	NPD4625	Phase 3
0.8146	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD7768	Phase 2
0.7943	Intermediate Similarity	NPD5124	Phase 1
0.7943	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD3027	Phase 3
0.7885	Intermediate Similarity	NPD6959	Discontinued
0.7877	Intermediate Similarity	NPD7466	Approved
0.7857	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1549	Phase 2
0.7727	Intermediate Similarity	NPD8455	Phase 2
0.7721	Intermediate Similarity	NPD422	Phase 1
0.7667	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3750	Approved
0.7625	Intermediate Similarity	NPD6166	Phase 2
0.7625	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6582	Phase 2
0.7609	Intermediate Similarity	NPD6583	Phase 3
0.7603	Intermediate Similarity	NPD6099	Approved
0.7603	Intermediate Similarity	NPD6100	Approved
0.7597	Intermediate Similarity	NPD7411	Suspended
0.7582	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6584	Phase 3
0.7568	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8651	Approved
0.755	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2796	Approved
0.7483	Intermediate Similarity	NPD6798	Discontinued
0.7482	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7097	Phase 1
0.7464	Intermediate Similarity	NPD1091	Approved
0.7463	Intermediate Similarity	NPD6671	Approved
0.7436	Intermediate Similarity	NPD1934	Approved
0.7425	Intermediate Similarity	NPD8053	Approved
0.7425	Intermediate Similarity	NPD8054	Approved
0.7419	Intermediate Similarity	NPD4380	Phase 2
0.7415	Intermediate Similarity	NPD1510	Phase 2
0.7402	Intermediate Similarity	NPD940	Approved
0.7402	Intermediate Similarity	NPD846	Approved
0.74	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3892	Phase 2
0.7389	Intermediate Similarity	NPD7819	Suspended
0.7378	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2797	Approved
0.7368	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7041	Phase 2
0.7368	Intermediate Similarity	NPD7843	Approved
0.7368	Intermediate Similarity	NPD5535	Approved
0.7358	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3749	Approved
0.7358	Intermediate Similarity	NPD7075	Discontinued
0.7347	Intermediate Similarity	NPD4536	Approved
0.7347	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4538	Approved
0.7347	Intermediate Similarity	NPD2200	Suspended
0.7333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7157	Approved
0.7333	Intermediate Similarity	NPD1652	Phase 2
0.7329	Intermediate Similarity	NPD6355	Discontinued
0.7328	Intermediate Similarity	NPD2684	Approved
0.7319	Intermediate Similarity	NPD5846	Approved
0.7319	Intermediate Similarity	NPD6516	Phase 2
0.7308	Intermediate Similarity	NPD968	Approved
0.7297	Intermediate Similarity	NPD3748	Approved
0.7297	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5451	Approved
0.7273	Intermediate Similarity	NPD5844	Phase 1
0.7273	Intermediate Similarity	NPD3018	Phase 2
0.7273	Intermediate Similarity	NPD4750	Phase 3
0.7273	Intermediate Similarity	NPD8156	Discontinued
0.7267	Intermediate Similarity	NPD7037	Approved
0.726	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1240	Approved
0.7252	Intermediate Similarity	NPD290	Approved
0.7244	Intermediate Similarity	NPD3020	Approved
0.7241	Intermediate Similarity	NPD3268	Approved
0.7234	Intermediate Similarity	NPD5327	Phase 3
0.7229	Intermediate Similarity	NPD7074	Phase 3
0.7222	Intermediate Similarity	NPD7199	Phase 2
0.7219	Intermediate Similarity	NPD6674	Discontinued
0.7212	Intermediate Similarity	NPD8251	Approved
0.7212	Intermediate Similarity	NPD8099	Discontinued
0.7212	Intermediate Similarity	NPD8252	Approved
0.7212	Intermediate Similarity	NPD7228	Approved
0.7211	Intermediate Similarity	NPD5735	Approved
0.7202	Intermediate Similarity	NPD7549	Discontinued
0.7192	Intermediate Similarity	NPD6233	Phase 2
0.7185	Intermediate Similarity	NPD5283	Phase 1
0.7183	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3225	Approved
0.7181	Intermediate Similarity	NPD5588	Approved
0.7181	Intermediate Similarity	NPD5960	Phase 3
0.7178	Intermediate Similarity	NPD7229	Phase 3
0.7174	Intermediate Similarity	NPD6581	Approved
0.7174	Intermediate Similarity	NPD6580	Approved
0.717	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7054	Approved
0.7162	Intermediate Similarity	NPD1607	Approved
0.716	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD4140	Approved
0.7134	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7126	Intermediate Similarity	NPD7472	Approved
0.7123	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7119	Phase 2
0.7113	Intermediate Similarity	NPD2982	Phase 2
0.7113	Intermediate Similarity	NPD2983	Phase 2
0.7107	Intermediate Similarity	NPD37	Approved
0.7101	Intermediate Similarity	NPD7808	Phase 3
0.7099	Intermediate Similarity	NPD6234	Discontinued
0.7086	Intermediate Similarity	NPD7030	Discontinued
0.7083	Intermediate Similarity	NPD6797	Phase 2
0.7081	Intermediate Similarity	NPD4967	Phase 2
0.7081	Intermediate Similarity	NPD4965	Approved
0.7081	Intermediate Similarity	NPD7773	Phase 2
0.7081	Intermediate Similarity	NPD4966	Approved
0.7078	Intermediate Similarity	NPD6667	Approved
0.7078	Intermediate Similarity	NPD5058	Phase 3
0.7078	Intermediate Similarity	NPD6666	Approved
0.7078	Intermediate Similarity	NPD6815	Approved
0.7075	Intermediate Similarity	NPD7265	Discontinued
0.7073	Intermediate Similarity	NPD3787	Discontinued
0.707	Intermediate Similarity	NPD1653	Approved
0.7067	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2801	Approved
0.7059	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD8312	Approved
0.7059	Intermediate Similarity	NPD7003	Approved
0.7055	Intermediate Similarity	NPD7095	Approved
0.7054	Intermediate Similarity	NPD1242	Phase 1
0.705	Intermediate Similarity	NPD7741	Discontinued
0.7047	Intermediate Similarity	NPD6353	Approved
0.7047	Intermediate Similarity	NPD4097	Suspended
0.7042	Intermediate Similarity	NPD1608	Approved
0.7042	Intermediate Similarity	NPD2981	Phase 2
0.7041	Intermediate Similarity	NPD7251	Discontinued
0.7039	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1511	Approved
0.7032	Intermediate Similarity	NPD6799	Approved
0.7008	Intermediate Similarity	NPD2860	Approved
0.7008	Intermediate Similarity	NPD2859	Approved
0.7006	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3445	Approved
0.7	Intermediate Similarity	NPD6801	Discontinued
0.7	Intermediate Similarity	NPD3444	Approved
0.7	Intermediate Similarity	NPD3443	Approved
0.7	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3685	Discontinued
0.6987	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD821	Approved
0.6981	Remote Similarity	NPD6599	Discontinued
0.6975	Remote Similarity	NPD3882	Suspended
0.6974	Remote Similarity	NPD5762	Approved
0.6974	Remote Similarity	NPD6004	Phase 3
0.6974	Remote Similarity	NPD5763	Approved
0.6974	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6005	Phase 3
0.6974	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6002	Phase 3
0.6966	Remote Similarity	NPD3691	Phase 2
0.6966	Remote Similarity	NPD3690	Phase 2
0.6959	Remote Similarity	NPD7477	Discontinued
0.6957	Remote Similarity	NPD2557	Approved
0.695	Remote Similarity	NPD2667	Approved
0.695	Remote Similarity	NPD2668	Approved
0.6944	Remote Similarity	NPD6696	Suspended
0.6943	Remote Similarity	NPD1512	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