NPASS Compound

Natural Product: NPC479431

Natural Product ID	NPC479431
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZLJNDEAZTHKUBC-QNZWHCBBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 104109 0 0 0 0 0 0 0 0999 V2000 -8.1793 -2.2084 -1.0548 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4628 -1.0803 -0.2487 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9116 0.1848 -0.8662 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8748 1.2290 -0.7787 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9013 1.0810 0.3819 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0430 2.3059 0.3575 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6343 2.1267 0.8008 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9732 1.0783 0.0031 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7614 1.6263 -1.3946 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7827 -0.1907 -0.0615 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1600 -1.2681 -0.5000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7325 -1.3258 -0.9298 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9544 -0.1446 -0.4902 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5282 -0.4079 -0.2669 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8384 -1.4421 0.7279 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0408 -0.8570 -1.6220 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5039 -1.0499 -1.5691 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3082 -0.1331 -0.7364 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5902 1.0465 -0.1566 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2403 1.3475 1.2029 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9483 2.2578 -1.0117 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1352 0.9538 -0.0502 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6068 1.4958 1.2603 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8573 1.8376 1.0414 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6277 0.6156 0.5915 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9103 -0.1745 1.8475 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8991 -0.8845 0.3085 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3126 -1.0583 0.4086 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9329 -0.4868 -0.5060 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7827 -1.8337 1.5044 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0160 -2.0618 1.8073 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1625 -1.5673 1.1209 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2669 -2.4504 1.0879 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4768 -2.1209 0.5785 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6862 -0.8562 0.0497 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6420 0.0281 0.0651 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3993 -0.3347 0.5992 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8142 1.2883 -0.4498 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7415 2.2015 -0.4358 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9437 -0.5725 -0.4607 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9446 -0.9899 -2.9248 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2067 -0.2322 0.3699 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9827 -1.3410 -0.2711 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8160 -2.6540 0.5175 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6419 -1.5238 -1.6138 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7356 1.2309 1.6366 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6298 0.3298 2.4958 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5700 2.3151 1.8126 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5988 -2.4617 -1.9497 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2594 -3.1183 -0.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2075 -1.8888 -1.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8550 -1.2641 0.7851 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1020 0.0018 -1.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9020 0.4882 -0.4539 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3270 1.3962 -1.7369 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3949 2.2142 -0.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4736 3.0968 1.0521 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1452 2.8173 -0.6409 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1152 3.1052 0.5826 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6196 2.0346 1.8855 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5802 2.2958 -1.7339 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 0.8302 -2.1714 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8663 2.3077 -1.4304 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7193 -2.1952 -0.5598 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7545 -1.3678 -2.0389 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2646 -2.3002 -0.6369 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9105 0.5558 -1.3890 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3892 -1.0476 1.6034 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0208 -2.0153 1.1277 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5058 -2.2143 0.2922 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7687 -0.0949 -2.3909 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5742 -1.8435 -1.9140 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7198 -2.1312 -1.3087 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1739 0.2234 -1.3669 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2481 2.4573 1.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7115 0.9016 2.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3073 1.0458 1.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1658 2.3684 -1.7963 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9445 2.1269 -1.4677 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9024 3.1857 -0.3980 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6486 1.6057 -0.8402 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6709 0.7897 2.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1335 2.4383 1.5314 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9469 2.6845 0.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2499 2.1686 2.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0842 -0.0594 2.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1722 -1.2182 1.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7915 0.2647 2.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0033 -2.2935 2.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2083 -2.7209 2.7193 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1590 -3.4619 1.4910 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2933 -2.8316 0.5749 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6614 0.4536 0.6430 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4432 2.3412 0.6231 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0227 3.1802 -0.8869 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8764 1.8039 -0.9958 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0814 -0.2371 -1.4043 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7868 -1.8378 -3.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1675 -0.5576 1.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7703 -2.9211 1.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6428 -3.5168 -0.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0824 -2.5333 1.3392 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2434 -0.9598 -2.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8128 2.5785 2.7552 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 18 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 35 40 1 0 17 41 1 0 10 42 1 0 42 43 1 0 43 44 1 0 43 45 1 6 5 46 1 1 46 47 2 0 46 48 1 0 43 2 1 0 42 5 1 0 25 8 1 0 37 32 1 0 25 13 1 0 22 14 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 1 3 53 1 0 3 54 1 0 4 55 1 0 4 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 7 60 1 0 9 61 1 0 9 62 1 0 9 63 1 0 11 64 1 0 12 65 1 0 12 66 1 0 13 67 1 6 15 68 1 0 15 69 1 0 15 70 1 0 16 71 1 0 16 72 1 0 17 73 1 1 18 74 1 6 20 75 1 0 20 76 1 0 20 77 1 0 21 78 1 0 21 79 1 0 21 80 1 0 22 81 1 6 23 82 1 0 23 83 1 0 24 84 1 0 24 85 1 0 26 86 1 0 26 87 1 0 26 88 1 0 30 89 1 0 31 90 1 0 33 91 1 0 34 92 1 0 37 93 1 0 39 94 1 0 39 95 1 0 39 96 1 0 40 97 1 0 41 98 1 0 42 99 1 1 44100 1 0 44101 1 0 44102 1 0 45103 1 0 48104 1 0 M END

Standard InCHIKey	ZLJNDEAZTHKUBC-QNZWHCBBSA-N
Standard InCHI	InChI=1S/C40H56O8/c1-23-15-18-40(34(44)45)20-19-37(5)25(32(40)39(23,7)46)11-13-30-36(4)22-27(42)33(35(2,3)29(36)16-17-38(30,37)6)48-31(43)14-10-24-9-12-26(41)28(21-24)47-8/h9-12,14,21,23,27,29-30,32-33,41-42,46H,13,15-20,22H2,1-8H3,(H,44,45)/b14-10-/t23-,27-,29+,30-,32-,33+,36+,37-,38-,39-,40+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)/C=Cc3ccc(c(c3)OC)O)O)[C@@H]2[C@]1(C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	664.4	Volume:	700.924 ? Van der Waals volume.
Dense:	0.948	LogP:	3.534 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.157 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.726 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
TPSA:	133.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.148	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.227	Fsp³:	0.7
MCE-18:	172.235 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.947	Fluc inhibitor:	0.971 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.178 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.09 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.086	Promiscuous compounds:	0.146

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.427	MDCK Permeability:	-5.038
Pgp-inhibitor:	0.192	Pgp-substrate:	0.0
PAMPA:	0.965 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.95	30% Bioavailability (F30%):	0.817
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.428
Plasma Protein Binding (PPB):	84.744%	Volume Distribution (VD):	-0.131
Fu:	13.556% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.443
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.175	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.989
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

3.258

Half-life (T1/2):

1.628

ADMET: Toxicity

hERG Blockers:	0.07	hERG Blockers (10um):	0.132
Human Hepatotoxicity (H-HT):	0.671	Drug-induced Liver Injury (DILI):	0.173
AMES Toxicity:	0.157	Rat Oral Acute Toxicity:	0.197
Maximum Recommended Daily Dose:	0.567	Skin Sensitization:	0.999
Carcinogencity:	0.248	Eye Corrosion:	0.001
Eye Irritation:	0.184	Respiratory Toxicity:	0.858
Drug-induced Neurotoxicity:	0.02	Ototoxicity:	0.512
Hematotoxicity:	0.054	Drug-induced Nephrotoxicity:	0.85
Genotoxicity:	0.076	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	0.908	Hek293 Cytotoxicity:	0.699
BCF:	1.218 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.303 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.966 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.308 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	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	Organism Name	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	1

Activity Type	# Activity
Cell line	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell line	BV-2	Mus musculus	IC50	=	37100.0	nM	PMID[28358502]
NPT34	Cell line	BV-2	Mus musculus	Activity	=	110.9	%	PMID[28358502]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC479431 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5666
0.1-0.2	38193
0.2-0.3	5300
0.3-0.4	549
0.4-0.5	80
0.5-0.6	45
0.6-0.7	10
0.7-0.8	0
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC481234
0.8587	High Similarity	NPC25491
0.8404	Intermediate Similarity	NPC482051
0.8351	Intermediate Similarity	NPC118033
0.8247	Intermediate Similarity	NPC601567
0.8247	Intermediate Similarity	NPC606631
0.8	Intermediate Similarity	NPC481235
0.71	Intermediate Similarity	NPC304110
0.71	Intermediate Similarity	NPC27518
0.71	Intermediate Similarity	NPC611516
0.7	Intermediate Similarity	NPC482052
0.7	Intermediate Similarity	NPC605663
0.6923	Remote Similarity	NPC233012
0.6796	Remote Similarity	NPC610795
0.6538	Remote Similarity	NPC178093
0.6535	Remote Similarity	NPC171007
0.6535	Remote Similarity	NPC190849
0.6415	Remote Similarity	NPC479745
0.6381	Remote Similarity	NPC482049
0.6381	Remote Similarity	NPC482050
0.6321	Remote Similarity	NPC324798
0.6321	Remote Similarity	NPC479742
0.5741	Remote Similarity	NPC172311
0.5701	Remote Similarity	NPC101863
0.5664	Remote Similarity	NPC310729
0.5664	Remote Similarity	NPC150310
0.5575	Remote Similarity	NPC206232
0.5575	Remote Similarity	NPC14515
0.5556	Remote Similarity	NPC22676
0.5545	Remote Similarity	NPC205392
0.5545	Remote Similarity	NPC105942
0.5505	Remote Similarity	NPC470618
0.5505	Remote Similarity	NPC470619
0.5455	Remote Similarity	NPC230151
0.5455	Remote Similarity	NPC479744
0.54	Remote Similarity	NPC54909
0.5357	Remote Similarity	NPC479739
0.5327	Remote Similarity	NPC173569
0.5278	Remote Similarity	NPC475138
0.5268	Remote Similarity	NPC132126
0.5258	Remote Similarity	NPC247139
0.5248	Remote Similarity	NPC327179
0.5234	Remote Similarity	NPC485587
0.5229	Remote Similarity	NPC477874
0.5221	Remote Similarity	NPC479747
0.5221	Remote Similarity	NPC479746
0.5217	Remote Similarity	NPC479740
0.5217	Remote Similarity	NPC479741
0.5204	Remote Similarity	NPC62516
0.5179	Remote Similarity	NPC488214
0.5175	Remote Similarity	NPC473773
0.5175	Remote Similarity	NPC475579
0.5155	Remote Similarity	NPC259733
0.5155	Remote Similarity	NPC158371
0.5155	Remote Similarity	NPC207922
0.5155	Remote Similarity	NPC202728
0.5155	Remote Similarity	NPC158059
0.5152	Remote Similarity	NPC157113
0.5135	Remote Similarity	NPC477873
0.513	Remote Similarity	NPC475454
0.513	Remote Similarity	NPC473579
0.5102	Remote Similarity	NPC132824
0.5089	Remote Similarity	NPC198621
0.5089	Remote Similarity	NPC216940
0.5086	Remote Similarity	NPC473680
0.5051	Remote Similarity	NPC148964
0.5043	Remote Similarity	NPC475311

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC479431 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2976
0.1-0.2	6037
0.2-0.3	135
0.3-0.4	1
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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