NPASS Compound

Structure

NPC470955 OpenBabel07101718222D 23 25 0 0 1 0 0 0 0 0999 V2000 3.3052 -2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6742 -1.8827 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 -0.8660 -0.5000 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 -0.0000 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 -1.7321 2.0000 0.0000 C 0 0 0 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 19 1 6 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 6 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 20 1 0 0 0 0 17 23 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.17
Volume:	304.17
LogP:	1.444
LogD:	0.762
LogS:	-2.753
# Rotatable Bonds:	1
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.806
Synthetic Accessibility Score:	4.1
Fsp3:	0.824
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:	-5.157
MDCK Permeability:	2.648781446623616e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.463
Plasma Protein Binding (PPB):	67.41468048095703%
Volume Distribution (VD):	0.335
Pgp-substrate:	28.631019592285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.709
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.748
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.775
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.111

ADMET: Excretion

Clearance (CL):	1.951
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.22
Maximum Recommended Daily Dose:	0.095
Skin Sensitization:	0.053
Carcinogencity:	0.087
Eye Corrosion:	0.048
Eye Irritation:	0.632
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC470955

Natural Product ID:	NPC470955
*Common Name:**	Kravanhin D
IUPAC Name:	(4aS,4bR,8aS,10aS)-8-hydroxy-7-(2-hydroxyethyl)-1,1,4a,8a-tetramethyl-2,3,4,4b,5,8,10,10a-octahydrophenanthren-9-one
Synonyms:	Kravanhin D
Standard InCHIKey:	KTDOLCHRZYHEBZ-KCDHOOEKSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-18(2)9-5-10-19(3)14-7-6-13(8-11-21)17(23)20(14,4)16(22)12-15(18)19/h6,14-15,17,21,23H,5,7-12H2,1-4H3/t14-,15+,17?,19-,20-/m1/s1
SMILES:	OCCC1=CC[C@H]2[C@](C1O)(C)C(=O)C[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333383
PubChem CID:	71718232
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO31457	Amomum kravanh	Species	Zingiberaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23394284]
NPO31457	Amomum kravanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31457	Amomum kravanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	10.0	%	PMID[545950]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	90.0	%	PMID[545950]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	200000.0	nM	PMID[545950]

☑ 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 NPC470955 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	178
0.1-0.2	1110
0.2-0.3	4376
0.3-0.4	11421
0.4-0.5	11854
0.5-0.6	6501
0.6-0.7	5007
0.7-0.8	2043
0.8-0.85	178
0.85-0.9	27
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9012	High Similarity	NPC148685
0.9012	High Similarity	NPC157895
0.9012	High Similarity	NPC104120
0.8929	High Similarity	NPC274724
0.8929	High Similarity	NPC471224
0.8902	High Similarity	NPC14151
0.8851	High Similarity	NPC48010
0.8824	High Similarity	NPC82979
0.8824	High Similarity	NPC322159
0.881	High Similarity	NPC227132
0.878	High Similarity	NPC2482
0.8736	High Similarity	NPC472970
0.8736	High Similarity	NPC472971
0.8706	High Similarity	NPC476426
0.8706	High Similarity	NPC474083
0.8642	High Similarity	NPC74995
0.8621	High Similarity	NPC53911
0.8621	High Similarity	NPC471791
0.8621	High Similarity	NPC471793
0.8621	High Similarity	NPC328313
0.8605	High Similarity	NPC472985
0.8605	High Similarity	NPC473226
0.8605	High Similarity	NPC472986
0.8605	High Similarity	NPC194417
0.8605	High Similarity	NPC472974
0.8605	High Similarity	NPC469994
0.8588	High Similarity	NPC59453
0.8588	High Similarity	NPC476412
0.8588	High Similarity	NPC180834
0.8588	High Similarity	NPC221758
0.8571	High Similarity	NPC310989
0.8571	High Similarity	NPC48362
0.8571	High Similarity	NPC151519
0.8571	High Similarity	NPC212083
0.8539	High Similarity	NPC73457
0.8537	High Similarity	NPC297996
0.8523	High Similarity	NPC473999
0.8523	High Similarity	NPC472973
0.8523	High Similarity	NPC2983
0.8523	High Similarity	NPC69627
0.8523	High Similarity	NPC472983
0.8523	High Similarity	NPC309603
0.8523	High Similarity	NPC281524
0.8506	High Similarity	NPC475740
0.8506	High Similarity	NPC73064
0.8506	High Similarity	NPC298904
0.8506	High Similarity	NPC272039
0.8506	High Similarity	NPC220930
0.8488	Intermediate Similarity	NPC474853
0.8488	Intermediate Similarity	NPC179006
0.8488	Intermediate Similarity	NPC133954
0.8462	Intermediate Similarity	NPC53565
0.8452	Intermediate Similarity	NPC121984
0.8452	Intermediate Similarity	NPC3915
0.8444	Intermediate Similarity	NPC477520
0.8444	Intermediate Similarity	NPC474736
0.8434	Intermediate Similarity	NPC281138
0.8434	Intermediate Similarity	NPC308038
0.8434	Intermediate Similarity	NPC152061
0.8427	Intermediate Similarity	NPC69622
0.8421	Intermediate Similarity	NPC90177
0.8415	Intermediate Similarity	NPC91594
0.8409	Intermediate Similarity	NPC1753
0.8409	Intermediate Similarity	NPC474511
0.8391	Intermediate Similarity	NPC145879
0.8391	Intermediate Similarity	NPC475862
0.8391	Intermediate Similarity	NPC31564
0.8391	Intermediate Similarity	NPC51014
0.8391	Intermediate Similarity	NPC474733
0.8391	Intermediate Similarity	NPC74363
0.8391	Intermediate Similarity	NPC474732
0.8391	Intermediate Similarity	NPC213412
0.8391	Intermediate Similarity	NPC474778
0.8391	Intermediate Similarity	NPC198761
0.8387	Intermediate Similarity	NPC174663
0.8372	Intermediate Similarity	NPC85774
0.8372	Intermediate Similarity	NPC214043
0.8372	Intermediate Similarity	NPC473157
0.8372	Intermediate Similarity	NPC82902
0.8352	Intermediate Similarity	NPC472976
0.8352	Intermediate Similarity	NPC292793
0.8352	Intermediate Similarity	NPC148964
0.8352	Intermediate Similarity	NPC472977
0.8333	Intermediate Similarity	NPC172013
0.8333	Intermediate Similarity	NPC38754
0.8333	Intermediate Similarity	NPC472978
0.8333	Intermediate Similarity	NPC473998
0.8333	Intermediate Similarity	NPC6255
0.8333	Intermediate Similarity	NPC471588
0.8333	Intermediate Similarity	NPC306095
0.8333	Intermediate Similarity	NPC475806
0.8315	Intermediate Similarity	NPC1015
0.8315	Intermediate Similarity	NPC474245
0.8315	Intermediate Similarity	NPC472477
0.8315	Intermediate Similarity	NPC472475
0.8315	Intermediate Similarity	NPC32830
0.8315	Intermediate Similarity	NPC31985
0.8315	Intermediate Similarity	NPC469319
0.8315	Intermediate Similarity	NPC229871
0.8313	Intermediate Similarity	NPC239098
0.8313	Intermediate Similarity	NPC475994
0.8295	Intermediate Similarity	NPC58063
0.8295	Intermediate Similarity	NPC317590
0.8295	Intermediate Similarity	NPC173089
0.8295	Intermediate Similarity	NPC158141
0.8295	Intermediate Similarity	NPC96496
0.8295	Intermediate Similarity	NPC71507
0.8293	Intermediate Similarity	NPC263582
0.8276	Intermediate Similarity	NPC255174
0.8276	Intermediate Similarity	NPC474218
0.8276	Intermediate Similarity	NPC469948
0.8276	Intermediate Similarity	NPC470574
0.8261	Intermediate Similarity	NPC271195
0.8256	Intermediate Similarity	NPC105173
0.8247	Intermediate Similarity	NPC166607
0.8242	Intermediate Similarity	NPC109305
0.8242	Intermediate Similarity	NPC472930
0.8242	Intermediate Similarity	NPC69454
0.8242	Intermediate Similarity	NPC472942
0.8235	Intermediate Similarity	NPC116797
0.8235	Intermediate Similarity	NPC476646
0.8235	Intermediate Similarity	NPC473420
0.8229	Intermediate Similarity	NPC95899
0.8222	Intermediate Similarity	NPC86372
0.8222	Intermediate Similarity	NPC193750
0.8222	Intermediate Similarity	NPC172361
0.8222	Intermediate Similarity	NPC320026
0.8214	Intermediate Similarity	NPC474113
0.8202	Intermediate Similarity	NPC206060
0.8202	Intermediate Similarity	NPC471724
0.8202	Intermediate Similarity	NPC471722
0.8202	Intermediate Similarity	NPC17733
0.8202	Intermediate Similarity	NPC470417
0.8202	Intermediate Similarity	NPC474512
0.8202	Intermediate Similarity	NPC290690
0.8202	Intermediate Similarity	NPC470629
0.8202	Intermediate Similarity	NPC181225
0.8202	Intermediate Similarity	NPC473242
0.8202	Intermediate Similarity	NPC472802
0.8193	Intermediate Similarity	NPC325946
0.8193	Intermediate Similarity	NPC197659
0.8191	Intermediate Similarity	NPC478056
0.8191	Intermediate Similarity	NPC316598
0.8182	Intermediate Similarity	NPC262085
0.8182	Intermediate Similarity	NPC325594
0.8182	Intermediate Similarity	NPC73038
0.8182	Intermediate Similarity	NPC158393
0.8182	Intermediate Similarity	NPC94666
0.8182	Intermediate Similarity	NPC477579
0.8182	Intermediate Similarity	NPC95594
0.8182	Intermediate Similarity	NPC20688
0.8182	Intermediate Similarity	NPC155011
0.8182	Intermediate Similarity	NPC235341
0.8182	Intermediate Similarity	NPC473168
0.8172	Intermediate Similarity	NPC116457
0.8172	Intermediate Similarity	NPC235053
0.8172	Intermediate Similarity	NPC132824
0.8161	Intermediate Similarity	NPC161423
0.8161	Intermediate Similarity	NPC227064
0.8161	Intermediate Similarity	NPC329043
0.8161	Intermediate Similarity	NPC321187
0.8161	Intermediate Similarity	NPC165064
0.8161	Intermediate Similarity	NPC58841
0.8161	Intermediate Similarity	NPC473246
0.8152	Intermediate Similarity	NPC209868
0.8152	Intermediate Similarity	NPC8993
0.8152	Intermediate Similarity	NPC474690
0.8152	Intermediate Similarity	NPC474529
0.8152	Intermediate Similarity	NPC474882
0.8144	Intermediate Similarity	NPC160843
0.8144	Intermediate Similarity	NPC474281
0.814	Intermediate Similarity	NPC93590
0.814	Intermediate Similarity	NPC145143
0.814	Intermediate Similarity	NPC46881
0.814	Intermediate Similarity	NPC110780
0.8132	Intermediate Similarity	NPC282616
0.8132	Intermediate Similarity	NPC228784
0.8132	Intermediate Similarity	NPC155120
0.8132	Intermediate Similarity	NPC63748
0.8132	Intermediate Similarity	NPC288833
0.8132	Intermediate Similarity	NPC324341
0.8132	Intermediate Similarity	NPC105189
0.8132	Intermediate Similarity	NPC966
0.8132	Intermediate Similarity	NPC233116
0.8132	Intermediate Similarity	NPC472975
0.8132	Intermediate Similarity	NPC187722
0.8125	Intermediate Similarity	NPC136289
0.8125	Intermediate Similarity	NPC34834
0.8118	Intermediate Similarity	NPC472478
0.8118	Intermediate Similarity	NPC96362
0.8111	Intermediate Similarity	NPC25906
0.8111	Intermediate Similarity	NPC198664
0.8111	Intermediate Similarity	NPC64872
0.8111	Intermediate Similarity	NPC186688
0.8111	Intermediate Similarity	NPC26959
0.8111	Intermediate Similarity	NPC76879
0.8111	Intermediate Similarity	NPC474700
0.8111	Intermediate Similarity	NPC274330
0.8111	Intermediate Similarity	NPC472688
0.8111	Intermediate Similarity	NPC143232

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 NPC470955 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1449
0.2-0.3	3716
0.3-0.4	2513
0.4-0.5	810
0.5-0.6	201
0.6-0.7	223
0.7-0.8	67
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8588	High Similarity	NPD4786	Approved
0.8571	High Similarity	NPD3667	Approved
0.8182	Intermediate Similarity	NPD3618	Phase 1
0.8161	Intermediate Similarity	NPD3133	Approved
0.8161	Intermediate Similarity	NPD3665	Phase 1
0.8161	Intermediate Similarity	NPD3666	Approved
0.8111	Intermediate Similarity	NPD5328	Approved
0.7935	Intermediate Similarity	NPD7515	Phase 2
0.7935	Intermediate Similarity	NPD6079	Approved
0.7849	Intermediate Similarity	NPD4202	Approved
0.7849	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD4519	Discontinued
0.7778	Intermediate Similarity	NPD4623	Approved
0.7753	Intermediate Similarity	NPD3668	Phase 3
0.7701	Intermediate Similarity	NPD4695	Discontinued
0.7582	Intermediate Similarity	NPD5279	Phase 3
0.7582	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7748	Approved
0.7576	Intermediate Similarity	NPD5211	Phase 2
0.7529	Intermediate Similarity	NPD7339	Approved
0.7529	Intermediate Similarity	NPD6942	Approved
0.7528	Intermediate Similarity	NPD4223	Phase 3
0.7528	Intermediate Similarity	NPD4221	Approved
0.7527	Intermediate Similarity	NPD4753	Phase 2
0.7526	Intermediate Similarity	NPD4755	Approved
0.7526	Intermediate Similarity	NPD7902	Approved
0.7473	Intermediate Similarity	NPD5329	Approved
0.7442	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5141	Approved
0.7423	Intermediate Similarity	NPD4697	Phase 3
0.7423	Intermediate Similarity	NPD5222	Approved
0.7423	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5221	Approved
0.7391	Intermediate Similarity	NPD6684	Approved
0.7391	Intermediate Similarity	NPD7146	Approved
0.7391	Intermediate Similarity	NPD5330	Approved
0.7391	Intermediate Similarity	NPD6409	Approved
0.7391	Intermediate Similarity	NPD7334	Approved
0.7391	Intermediate Similarity	NPD7521	Approved
0.7386	Intermediate Similarity	NPD7645	Phase 2
0.7374	Intermediate Similarity	NPD5286	Approved
0.7374	Intermediate Similarity	NPD4700	Approved
0.7374	Intermediate Similarity	NPD4696	Approved
0.7374	Intermediate Similarity	NPD5285	Approved
0.7368	Intermediate Similarity	NPD6411	Approved
0.7363	Intermediate Similarity	NPD4197	Approved
0.7347	Intermediate Similarity	NPD5173	Approved
0.7315	Intermediate Similarity	NPD7115	Discovery
0.7303	Intermediate Similarity	NPD7525	Registered
0.73	Intermediate Similarity	NPD5223	Approved
0.7292	Intermediate Similarity	NPD5779	Approved
0.7292	Intermediate Similarity	NPD5778	Approved
0.7283	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3617	Approved
0.7253	Intermediate Similarity	NPD4788	Approved
0.7234	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6903	Approved
0.7228	Intermediate Similarity	NPD5224	Approved
0.7228	Intermediate Similarity	NPD5226	Approved
0.7228	Intermediate Similarity	NPD4633	Approved
0.7228	Intermediate Similarity	NPD5225	Approved
0.7216	Intermediate Similarity	NPD7900	Approved
0.7216	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4138	Approved
0.7204	Intermediate Similarity	NPD4690	Approved
0.7204	Intermediate Similarity	NPD4693	Phase 3
0.7204	Intermediate Similarity	NPD5205	Approved
0.7204	Intermediate Similarity	NPD4689	Approved
0.7204	Intermediate Similarity	NPD4688	Approved
0.72	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD7639	Approved
0.7184	Intermediate Similarity	NPD7128	Approved
0.7184	Intermediate Similarity	NPD6675	Approved
0.7184	Intermediate Similarity	NPD6402	Approved
0.7184	Intermediate Similarity	NPD5739	Approved
0.7172	Intermediate Similarity	NPD6084	Phase 2
0.7172	Intermediate Similarity	NPD6083	Phase 2
0.7158	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6101	Approved
0.7158	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5174	Approved
0.7157	Intermediate Similarity	NPD4754	Approved
0.7157	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD4270	Approved
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD4269	Approved
0.7128	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8264	Approved
0.71	Intermediate Similarity	NPD4225	Approved
0.71	Intermediate Similarity	NPD7638	Approved
0.7079	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4634	Approved
0.7053	Intermediate Similarity	NPD6672	Approved
0.7053	Intermediate Similarity	NPD5737	Approved
0.7048	Intermediate Similarity	NPD7320	Approved
0.7048	Intermediate Similarity	NPD6881	Approved
0.7048	Intermediate Similarity	NPD6899	Approved
0.7021	Intermediate Similarity	NPD4694	Approved
0.7021	Intermediate Similarity	NPD5280	Approved
0.7021	Intermediate Similarity	NPD5690	Phase 2
0.7019	Intermediate Similarity	NPD4767	Approved
0.7019	Intermediate Similarity	NPD4768	Approved
0.7011	Intermediate Similarity	NPD6926	Approved
0.7011	Intermediate Similarity	NPD6924	Approved
0.701	Intermediate Similarity	NPD7637	Suspended
0.7	Intermediate Similarity	NPD6929	Approved
0.6981	Remote Similarity	NPD6373	Approved
0.6981	Remote Similarity	NPD6372	Approved
0.6952	Remote Similarity	NPD5701	Approved
0.6952	Remote Similarity	NPD5697	Approved
0.6952	Remote Similarity	NPD6412	Phase 2
0.6941	Remote Similarity	NPD4137	Phase 3
0.6923	Remote Similarity	NPD6930	Phase 2
0.6923	Remote Similarity	NPD4252	Approved
0.6923	Remote Similarity	NPD6931	Approved
0.6916	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD7102	Approved
0.6915	Remote Similarity	NPD5363	Approved
0.6914	Remote Similarity	NPD368	Approved
0.6907	Remote Similarity	NPD5785	Approved
0.6889	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4729	Approved
0.6887	Remote Similarity	NPD6011	Approved
0.6887	Remote Similarity	NPD5128	Approved
0.6887	Remote Similarity	NPD4730	Approved
0.686	Remote Similarity	NPD4747	Approved
0.686	Remote Similarity	NPD4244	Approved
0.686	Remote Similarity	NPD4691	Approved
0.686	Remote Similarity	NPD4245	Approved
0.6854	Remote Similarity	NPD6933	Approved
0.6852	Remote Similarity	NPD8130	Phase 1
0.6852	Remote Similarity	NPD6650	Approved
0.6852	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6617	Approved
0.6852	Remote Similarity	NPD6869	Approved
0.6852	Remote Similarity	NPD6649	Approved
0.6852	Remote Similarity	NPD6847	Approved
0.6848	Remote Similarity	NPD4692	Approved
0.6848	Remote Similarity	NPD4139	Approved
0.6842	Remote Similarity	NPD5786	Approved
0.6842	Remote Similarity	NPD6098	Approved
0.6837	Remote Similarity	NPD8035	Phase 2
0.6837	Remote Similarity	NPD5281	Approved
0.6837	Remote Similarity	NPD8034	Phase 2
0.6837	Remote Similarity	NPD5284	Approved
0.6824	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6014	Approved
0.6822	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD6012	Approved
0.6818	Remote Similarity	NPD4784	Approved
0.6818	Remote Similarity	NPD4785	Approved
0.6813	Remote Similarity	NPD4195	Approved
0.6809	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5695	Phase 3
0.6789	Remote Similarity	NPD6882	Approved
0.6789	Remote Similarity	NPD8297	Approved
0.6782	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4243	Approved
0.6782	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5776	Phase 2
0.6778	Remote Similarity	NPD6925	Approved
0.6774	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD3573	Approved
0.6765	Remote Similarity	NPD5696	Approved
0.6759	Remote Similarity	NPD5249	Phase 3
0.6759	Remote Similarity	NPD5169	Approved
0.6759	Remote Similarity	NPD5135	Approved
0.6759	Remote Similarity	NPD5250	Approved
0.6759	Remote Similarity	NPD5251	Approved
0.6759	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5247	Approved
0.6759	Remote Similarity	NPD5248	Approved
0.6744	Remote Similarity	NPD6922	Approved
0.6744	Remote Similarity	NPD6923	Approved
0.6744	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3698	Phase 2
0.6739	Remote Similarity	NPD7332	Phase 2
0.6739	Remote Similarity	NPD7514	Phase 3
0.6739	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7509	Discontinued
0.6737	Remote Similarity	NPD1696	Phase 3
0.6737	Remote Similarity	NPD1694	Approved
0.6729	Remote Similarity	NPD5168	Approved
0.6729	Remote Similarity	NPD6686	Approved
0.6703	Remote Similarity	NPD7145	Approved
0.6702	Remote Similarity	NPD5362	Discontinued
0.6702	Remote Similarity	NPD6695	Phase 3
0.6697	Remote Similarity	NPD5217	Approved
0.6697	Remote Similarity	NPD5215	Approved
0.6697	Remote Similarity	NPD5216	Approved
0.6697	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6902	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