NPASS Compound

Structure

NPC473090 OpenBabel07101719522D 27 28 0 0 1 0 0 0 0 0999 V2000 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 1 1 6 0 0 0 12 19 1 0 0 0 0 12 27 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 27 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 21 1 1 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	380.44
LogP:	2.88
LogD:	3.052
LogS:	-4.554
# Rotatable Bonds:	9
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	2.795
Fsp3:	0.35
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:	-4.676
MDCK Permeability:	5.640665767714381e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.232

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.576
Plasma Protein Binding (PPB):	73.43179321289062%
Volume Distribution (VD):	0.701
Pgp-substrate:	14.597967147827148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.299
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.744
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.536
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.223
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.744

ADMET: Excretion

Clearance (CL):	10.967
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.237
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.727
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.086
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.04
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC473090

Natural Product ID:	NPC473090
*Common Name:**	IZKLETPXYKZIMI-HXPMCKFVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IZKLETPXYKZIMI-HXPMCKFVSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-12(19(21)13-6-8-15(23-2)17(10-13)24-3)27-16-9-7-14(20(22)26-5)11-18(16)25-4/h6-12,19,21H,1-5H3/t12-,19+/m0/s1
SMILES:	COc1cc(ccc1O[C@H]([C@H](c1ccc(c(c1)OC)OC)O)C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609605
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20476749]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23713285]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[26296476]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26305406]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[29116780]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8666	Acorus tatarinowii	Species	Acoraceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	23300.0	nM	PMID[505802]

☑ 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 NPC473090 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	317
0.1-0.2	1319
0.2-0.3	3505
0.3-0.4	7844
0.4-0.5	10230
0.5-0.6	3723
0.6-0.7	5584
0.7-0.8	8546
0.8-0.85	1382
0.85-0.9	215
0.9-0.95	27
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC472969
0.9645	High Similarity	NPC476394
0.9645	High Similarity	NPC98809
0.9577	High Similarity	NPC473091
0.9493	High Similarity	NPC326065
0.9444	High Similarity	NPC75695
0.9433	High Similarity	NPC9370
0.9433	High Similarity	NPC287495
0.931	High Similarity	NPC36130
0.931	High Similarity	NPC134905
0.9252	High Similarity	NPC10205
0.9247	High Similarity	NPC137813
0.9225	High Similarity	NPC469683
0.9189	High Similarity	NPC471405
0.9184	High Similarity	NPC327032
0.9184	High Similarity	NPC191046
0.9184	High Similarity	NPC194095
0.9155	High Similarity	NPC469615
0.9103	High Similarity	NPC111785
0.9054	High Similarity	NPC469888
0.9044	High Similarity	NPC285776
0.9007	High Similarity	NPC203020
0.9007	High Similarity	NPC239966
0.9	High Similarity	NPC133984
0.8986	High Similarity	NPC283823
0.8986	High Similarity	NPC159418
0.8986	High Similarity	NPC157898
0.898	High Similarity	NPC243891
0.8958	High Similarity	NPC213900
0.894	High Similarity	NPC160780
0.894	High Similarity	NPC289811
0.8919	High Similarity	NPC267091
0.8913	High Similarity	NPC111888
0.8912	High Similarity	NPC205054
0.8904	High Similarity	NPC294972
0.8897	High Similarity	NPC98356
0.8897	High Similarity	NPC30890
0.8889	High Similarity	NPC239608
0.8889	High Similarity	NPC46161
0.8882	High Similarity	NPC53889
0.8882	High Similarity	NPC476373
0.8881	High Similarity	NPC184053
0.8874	High Similarity	NPC472860
0.8874	High Similarity	NPC226759
0.8874	High Similarity	NPC1913
0.8873	High Similarity	NPC289690
0.8873	High Similarity	NPC288452
0.8867	High Similarity	NPC300757
0.8867	High Similarity	NPC145425
0.8867	High Similarity	NPC180901
0.8865	High Similarity	NPC126206
0.8859	High Similarity	NPC131121
0.8844	High Similarity	NPC107636
0.8828	High Similarity	NPC113397
0.8824	High Similarity	NPC25389
0.8824	High Similarity	NPC311803
0.8824	High Similarity	NPC472859
0.8816	High Similarity	NPC87317
0.8803	High Similarity	NPC284409
0.8794	High Similarity	NPC471665
0.8794	High Similarity	NPC471664
0.8786	High Similarity	NPC144662
0.8786	High Similarity	NPC135127
0.8766	High Similarity	NPC476372
0.8766	High Similarity	NPC476371
0.8766	High Similarity	NPC285108
0.8766	High Similarity	NPC33298
0.8759	High Similarity	NPC160378
0.8759	High Similarity	NPC134975
0.8759	High Similarity	NPC2596
0.8758	High Similarity	NPC119125
0.8758	High Similarity	NPC24164
0.8758	High Similarity	NPC166277
0.875	High Similarity	NPC154275
0.875	High Similarity	NPC160512
0.875	High Similarity	NPC68324
0.875	High Similarity	NPC114179
0.875	High Similarity	NPC156818
0.875	High Similarity	NPC289322
0.875	High Similarity	NPC38779
0.8741	High Similarity	NPC474784
0.8733	High Similarity	NPC105827
0.8733	High Similarity	NPC44730
0.8733	High Similarity	NPC310661
0.8723	High Similarity	NPC139519
0.8714	High Similarity	NPC129889
0.8714	High Similarity	NPC307006
0.8707	High Similarity	NPC153620
0.8707	High Similarity	NPC24257
0.8701	High Similarity	NPC349525
0.8701	High Similarity	NPC103201
0.8701	High Similarity	NPC469889
0.8701	High Similarity	NPC473106
0.8696	High Similarity	NPC241354
0.8696	High Similarity	NPC226855
0.8696	High Similarity	NPC94810
0.8693	High Similarity	NPC74319
0.8693	High Similarity	NPC287872
0.869	High Similarity	NPC28326
0.8684	High Similarity	NPC88803
0.8684	High Similarity	NPC250436
0.8684	High Similarity	NPC291948
0.8684	High Similarity	NPC104983
0.8684	High Similarity	NPC300845
0.8681	High Similarity	NPC100675
0.8675	High Similarity	NPC25127
0.8671	High Similarity	NPC325625
0.8671	High Similarity	NPC207516
0.8667	High Similarity	NPC151425
0.8667	High Similarity	NPC93498
0.8667	High Similarity	NPC163883
0.8662	High Similarity	NPC90431
0.8662	High Similarity	NPC116745
0.8658	High Similarity	NPC227980
0.8654	High Similarity	NPC142614
0.8652	High Similarity	NPC237594
0.8652	High Similarity	NPC249791
0.8652	High Similarity	NPC476387
0.8652	High Similarity	NPC119060
0.8652	High Similarity	NPC155098
0.8652	High Similarity	NPC311339
0.8649	High Similarity	NPC98009
0.8645	High Similarity	NPC148273
0.8639	High Similarity	NPC291153
0.8639	High Similarity	NPC262282
0.8639	High Similarity	NPC287275
0.8639	High Similarity	NPC213482
0.8636	High Similarity	NPC472961
0.8636	High Similarity	NPC289346
0.8636	High Similarity	NPC472962
0.8636	High Similarity	NPC24627
0.8636	High Similarity	NPC292415
0.8633	High Similarity	NPC66905
0.863	High Similarity	NPC226738
0.863	High Similarity	NPC121573
0.863	High Similarity	NPC22176
0.863	High Similarity	NPC190587
0.863	High Similarity	NPC50954
0.8627	High Similarity	NPC470402
0.8627	High Similarity	NPC108456
0.8613	High Similarity	NPC475236
0.8609	High Similarity	NPC19380
0.8609	High Similarity	NPC199773
0.8609	High Similarity	NPC477231
0.8609	High Similarity	NPC146277
0.8609	High Similarity	NPC60211
0.8609	High Similarity	NPC474656
0.8609	High Similarity	NPC295646
0.8609	High Similarity	NPC289968
0.8609	High Similarity	NPC257648
0.8609	High Similarity	NPC60972
0.8609	High Similarity	NPC39732
0.8603	High Similarity	NPC109822
0.8603	High Similarity	NPC94276
0.8603	High Similarity	NPC221798
0.8601	High Similarity	NPC110899
0.8601	High Similarity	NPC112068
0.8601	High Similarity	NPC25305
0.8601	High Similarity	NPC95679
0.8601	High Similarity	NPC125417
0.86	High Similarity	NPC62354
0.86	High Similarity	NPC300329
0.8591	High Similarity	NPC474903
0.859	High Similarity	NPC100425
0.859	High Similarity	NPC45943
0.8582	High Similarity	NPC288743
0.8581	High Similarity	NPC299090
0.8581	High Similarity	NPC143892
0.8581	High Similarity	NPC229264
0.8581	High Similarity	NPC165389
0.8581	High Similarity	NPC283081
0.8581	High Similarity	NPC221383
0.8571	High Similarity	NPC275278
0.8571	High Similarity	NPC318799
0.8571	High Similarity	NPC207732
0.8571	High Similarity	NPC104854
0.8562	High Similarity	NPC473275
0.8562	High Similarity	NPC472916
0.8562	High Similarity	NPC470896
0.8562	High Similarity	NPC312256
0.8562	High Similarity	NPC318432
0.8562	High Similarity	NPC54928
0.8553	High Similarity	NPC472915
0.8553	High Similarity	NPC287504
0.8553	High Similarity	NPC18727
0.8553	High Similarity	NPC62051
0.8551	High Similarity	NPC281020
0.8551	High Similarity	NPC158654
0.8543	High Similarity	NPC228662
0.8543	High Similarity	NPC289438
0.8543	High Similarity	NPC31363
0.8533	High Similarity	NPC259576
0.8533	High Similarity	NPC306343
0.8533	High Similarity	NPC221091
0.8531	High Similarity	NPC475111
0.8531	High Similarity	NPC471719
0.8531	High Similarity	NPC156892
0.8529	High Similarity	NPC279379
0.8526	High Similarity	NPC90905
0.8526	High Similarity	NPC4013

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 NPC473090 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	834
0.2-0.3	1647
0.3-0.4	2437
0.4-0.5	1955
0.5-0.6	1112
0.6-0.7	651
0.7-0.8	213
0.8-0.85	21
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9014	High Similarity	NPD4628	Phase 3
0.8684	High Similarity	NPD4868	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD3817	Phase 2
0.8487	Intermediate Similarity	NPD1934	Approved
0.8446	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD3882	Suspended
0.8431	Intermediate Similarity	NPD2801	Approved
0.8375	Intermediate Similarity	NPD5844	Phase 1
0.8322	Intermediate Similarity	NPD230	Phase 1
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8312	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD6190	Approved
0.8301	Intermediate Similarity	NPD6385	Approved
0.8301	Intermediate Similarity	NPD6386	Approved
0.8299	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD9494	Approved
0.82	Intermediate Similarity	NPD6799	Approved
0.8194	Intermediate Similarity	NPD447	Suspended
0.8187	Intermediate Similarity	NPD6166	Phase 2
0.8187	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD7054	Approved
0.811	Intermediate Similarity	NPD7685	Pre-registration
0.8098	Intermediate Similarity	NPD7074	Phase 3
0.8098	Intermediate Similarity	NPD7472	Approved
0.8079	Intermediate Similarity	NPD1511	Approved
0.8077	Intermediate Similarity	NPD1465	Phase 2
0.8077	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD1608	Approved
0.8039	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD7075	Discontinued
0.8025	Intermediate Similarity	NPD5402	Approved
0.8013	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD7039	Approved
0.8	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7038	Approved
0.7986	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1512	Approved
0.7956	Intermediate Similarity	NPD9545	Approved
0.7952	Intermediate Similarity	NPD7808	Phase 3
0.795	Intermediate Similarity	NPD6232	Discontinued
0.7939	Intermediate Similarity	NPD6797	Phase 2
0.7937	Intermediate Similarity	NPD5494	Approved
0.7931	Intermediate Similarity	NPD6233	Phase 2
0.7925	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3027	Phase 3
0.7892	Intermediate Similarity	NPD7251	Discontinued
0.7885	Intermediate Similarity	NPD6599	Discontinued
0.7885	Intermediate Similarity	NPD4380	Phase 2
0.7881	Intermediate Similarity	NPD4110	Phase 3
0.7881	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6798	Discontinued
0.7852	Intermediate Similarity	NPD2935	Discontinued
0.7848	Intermediate Similarity	NPD7819	Suspended
0.7842	Intermediate Similarity	NPD17	Approved
0.7823	Intermediate Similarity	NPD6355	Discontinued
0.7808	Intermediate Similarity	NPD4062	Phase 3
0.7806	Intermediate Similarity	NPD5403	Approved
0.7805	Intermediate Similarity	NPD7473	Discontinued
0.78	Intermediate Similarity	NPD7266	Discontinued
0.7799	Intermediate Similarity	NPD5353	Approved
0.7791	Intermediate Similarity	NPD5242	Approved
0.7785	Intermediate Similarity	NPD37	Approved
0.7785	Intermediate Similarity	NPD2799	Discontinued
0.7778	Intermediate Similarity	NPD7199	Phase 2
0.7778	Intermediate Similarity	NPD8127	Discontinued
0.7754	Intermediate Similarity	NPD5536	Phase 2
0.775	Intermediate Similarity	NPD4967	Phase 2
0.775	Intermediate Similarity	NPD4966	Approved
0.775	Intermediate Similarity	NPD4965	Approved
0.7748	Intermediate Similarity	NPD1549	Phase 2
0.7742	Intermediate Similarity	NPD6273	Approved
0.7733	Intermediate Similarity	NPD2796	Approved
0.7722	Intermediate Similarity	NPD7411	Suspended
0.7712	Intermediate Similarity	NPD2354	Approved
0.7712	Intermediate Similarity	NPD3887	Approved
0.7707	Intermediate Similarity	NPD3226	Approved
0.7707	Intermediate Similarity	NPD3455	Phase 2
0.7706	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1933	Approved
0.7682	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD3146	Approved
0.7677	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5401	Approved
0.7674	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7033	Discontinued
0.7654	Intermediate Similarity	NPD6234	Discontinued
0.7654	Intermediate Similarity	NPD919	Approved
0.7647	Intermediate Similarity	NPD3750	Approved
0.7643	Intermediate Similarity	NPD1653	Approved
0.7635	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1613	Approved
0.7632	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2313	Discontinued
0.7619	Intermediate Similarity	NPD3764	Approved
0.7616	Intermediate Similarity	NPD1551	Phase 2
0.7603	Intermediate Similarity	NPD6832	Phase 2
0.7584	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6559	Discontinued
0.7571	Intermediate Similarity	NPD1894	Discontinued
0.7566	Intermediate Similarity	NPD2346	Discontinued
0.7558	Intermediate Similarity	NPD8434	Phase 2
0.7552	Intermediate Similarity	NPD1481	Phase 2
0.7552	Intermediate Similarity	NPD9269	Phase 2
0.7551	Intermediate Similarity	NPD7095	Approved
0.755	Intermediate Similarity	NPD1510	Phase 2
0.7548	Intermediate Similarity	NPD7440	Discontinued
0.7533	Intermediate Similarity	NPD6653	Approved
0.7532	Intermediate Similarity	NPD3687	Approved
0.7532	Intermediate Similarity	NPD3686	Approved
0.7518	Intermediate Similarity	NPD9268	Approved
0.7517	Intermediate Similarity	NPD1240	Approved
0.7517	Intermediate Similarity	NPD4060	Phase 1
0.7517	Intermediate Similarity	NPD1203	Approved
0.7516	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD1535	Discovery
0.747	Intermediate Similarity	NPD3926	Phase 2
0.7467	Intermediate Similarity	NPD4340	Discontinued
0.7466	Intermediate Similarity	NPD5647	Approved
0.7465	Intermediate Similarity	NPD1778	Approved
0.7464	Intermediate Similarity	NPD1241	Discontinued
0.7455	Intermediate Similarity	NPD1247	Approved
0.7452	Intermediate Similarity	NPD2534	Approved
0.7452	Intermediate Similarity	NPD2533	Approved
0.7452	Intermediate Similarity	NPD2532	Approved
0.7451	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2353	Approved
0.7451	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2344	Approved
0.744	Intermediate Similarity	NPD2163	Approved
0.744	Intermediate Similarity	NPD3751	Discontinued
0.744	Intermediate Similarity	NPD7228	Approved
0.7434	Intermediate Similarity	NPD3748	Approved
0.7434	Intermediate Similarity	NPD4308	Phase 3
0.7431	Intermediate Similarity	NPD9717	Approved
0.7431	Intermediate Similarity	NPD3972	Approved
0.7423	Intermediate Similarity	NPD7768	Phase 2
0.7419	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1607	Approved
0.7413	Intermediate Similarity	NPD3496	Discontinued
0.7407	Intermediate Similarity	NPD8455	Phase 2
0.7403	Intermediate Similarity	NPD4534	Discontinued
0.74	Intermediate Similarity	NPD943	Approved
0.7397	Intermediate Similarity	NPD2797	Approved
0.7394	Intermediate Similarity	NPD5585	Approved
0.7386	Intermediate Similarity	NPD6032	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7384	Intermediate Similarity	NPD8313	Approved
0.7383	Intermediate Similarity	NPD3268	Approved
0.7365	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD920	Approved
0.7342	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5283	Phase 1
0.7329	Intermediate Similarity	NPD1283	Approved
0.7329	Intermediate Similarity	NPD3225	Approved
0.7321	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD228	Approved
0.7308	Intermediate Similarity	NPD8166	Discontinued
0.7305	Intermediate Similarity	NPD3787	Discontinued
0.7297	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5049	Phase 3
0.729	Intermediate Similarity	NPD5958	Discontinued
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2979	Phase 3
0.7284	Intermediate Similarity	NPD6873	Phase 2
0.7279	Intermediate Similarity	NPD1358	Approved
0.7278	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2438	Suspended
0.7267	Intermediate Similarity	NPD2649	Approved
0.7267	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD2651	Approved
0.7261	Intermediate Similarity	NPD2309	Approved
0.7255	Intermediate Similarity	NPD7097	Phase 1
0.7246	Intermediate Similarity	NPD2821	Approved
0.7246	Intermediate Similarity	NPD6959	Discontinued
0.7244	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1652	Phase 2
0.7241	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3705	Approved
0.7239	Intermediate Similarity	NPD6844	Discontinued
0.7235	Intermediate Similarity	NPD7177	Discontinued
0.7233	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6004	Phase 3
0.7226	Intermediate Similarity	NPD2684	Approved
0.7226	Intermediate Similarity	NPD6005	Phase 3
0.7226	Intermediate Similarity	NPD5762	Approved
0.7226	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6003	Clinical (unspecified phase)

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